DEPARTMENT OF COMMERCE
BUREAU OF FOREIGN AND DOMESTIC COMMERCE
E. E. PRATT, Chief
SPECIAL AGENTS SERIES— No. 96
DYESTUFFS FOR AMERICAN TEXTILE
AND OTHER INDUSTRIES
THOMAS H. NORTON
Commercial Agent of the Department of Commerce
GOVERNMENT PRINTING OFFICE
DEPARTMENT OF COMMERCE
BUREAU OF FOREIGN AND DOMESTIC COMMERCE
E. E. PRATT, Chief
SPECIAL AGENTS SERIES— No. 96
DYESTUFFS FOR AMERICAN TEXTILE
AND OTHER INDUSTRIES
THOMAS H. NORTON
Commercial Agent of the Department of Commerce
GOVERNMENT PRINTING OFFICE
OF THIS PUBLICATION MAY BE PBOCURED FROM
THE SUPERINTENDENT OF DOCUMENTS
GOVERNMENT PRINTING OFFICE
WASHINGTON, D. C.
10 CENTS PER COPY
Letter of submittal 5
Dyestuff situation In the United States 12
I host nil's used in the United States 12
Natural organic dyes 12
Importation of natural organic dyes 14
Mineral dyes 15
Artificial organic dyes 15
Domestic manufacture of artificial dyestuffs 16
Foreign sources of artificial dyestuffs 17
Economic effects of dependence upon a single foreign source 17
Increased cost of coal-tar dyes 18
Outlook for the immediate future 18
Alternatives in case of a dyestuff famine 19
Outline of the coal-tar chemical industry 20
Coal-tar dye industry in the United States 21
Slow development of the American industry 21
American supply of raw materials 23
Coal tar from gas works 24
Coal tar and benzol from coke works 24
Present production of crude tar products 26
Price movement of American coal-tar crudes 28
Position of the American tar distiller 28
Supply of general chemicals required 29
The German coal-tar dyestuff industry 30
Trade in crudes and intermediates 31
Causes of Germany's supremacy 33
Research the chief cause 34
German industry, capital, dividends, etc 34
Geography of the German industry 35
Relations between companies 35
Equipment of plants 37
Wages in the German factories 37
Processes of manufacture 38
Uniformity of product 40
Typical phases 40
Illustrative outlines 41
Alizarin, naphthol yellow, magenta 41
Hydroquinone and synthetic indigo 42
The ketone dyes 44
Benzidine dyes 46
Tolidine and allied dyes 48
Patents in the German industry 48
American attitude toward the German industry 51
Producers of coal-tar crudes 52
Manufacturers of heavy chemicals 52
Manufacturers of artificial dyestuffs 52
Consumers of artificial dyestuffs 53
American Chemical Society, New York section 54
Establishment of an American industry 55
The problem in England and France 56
LETTER OF SUBMITTAL.
Department of Commerce,
Bureau of Foreign and Domestic Commerce,
Washington, March 20, 1915.
Sir: There is submitted herewith a report by Commercial Agent
Thomas H. Norton on dyes tuffs for American textile and other
industries. This report was called for by a resolution of the Senate,
under date of January 26, 1915. It presents fully the nature of the
dyestuffs used by American industries and the sources of supply,
showing the limited extent of the domestic manufacture and the
general dependence upon foreign-made dyes. The predominance of
Germany in this field is shown, and the reasons for this situation are
detailed. All factors connected with the creation of a self-contained,
independent, American coal-tar chemical industry are given in full,
and the problems involved by a threatened cessation of the present
foreign supply are considered.
E. E. Pratt,
Chief of Bureau.
To Hon. William C. Redfield,
Secretary of Commerce.
DYESTUFFS FOR AMERICAN TEXTILE AND OTHER
Under date of January 26, 1915, the Senate of the United States
passed the following resolution :
H< solved, That the Secretary of Commerce be, and he is hereby, directed to inform
the Senate as fully as possible as to the facts relating to the supply of dyestuffs for
American textile and other industries, the sources of such supply, the extent and
nature of the supply, the movement of prices, the available materials for the manu-
facture of such supplies in this country, the possibilities, if any, as to the stoppage of
such supply by reason of the existing European war, and any and all such other facts
aa will bring the existing conditions in the aniline color industry fully to the knowledge
of the Senate.
In response to this resolution, the Secretary of Commerce com-
municated to the Senate, under date of February 20, 1915, the fol-
lowing preliminary report, which summarizes the main facts and
outlines the scope of the full report as here given.
Numerous American industries are closely dependent upon the use
of dyestuffs. To the great textile branches they are almost as essen-
tial as their supplies of vegetable or animal fibers. The same con-
dition exists in the paint, varnish, and ink trades, the paper indus-
try, the feather and leather trades, and a group of minor industries,
dependent upon the products of these industries are a host of other
branches, all users of textiles. The old-time natural dyestuffs,
such as indigo, madder, cochineal, orchil, fustic, and a score more,
have no longer an extended use, with the exception of logwood,
which still plays a valued auxiliary role. The same is the case with
mineral colors, with some inconsiderable exceptions, such as Prus-
sian blue in silks and iron buff in khaki.
Artificial dyestuffs, derived from coal-tar products, have displaced
nearly all rivals, combining qualities of fastness, ease of application,
brilliancy, variety of shades, etc., utterly unknown to the former
generation of dyers.
EFFECT OF WAR ON DYE STUFF CONSUMERS.
The American consumption of artificial dyestuffs has attained an
annual value of $15,000,000, and grows steadily.
It is supplied partly by a domestic production valued at about
$3,000,000. This apparent domestic production is based chiefly upon
the use of foreign materials — half-made or nearly completed color
compounds. But a small portion is made from American crude coal-
8 DYESTUFFS FOR AMERICAN INDUSTRIES.
The great bulk of the artificial dyestuff supply comes from Europe.
The average imports are: From Germany, $7,850,000; Switzerland,
$910,000; Great Britain and others, $370,000; total, $9,130,000.
Since August 1, 1914, in consequence of the outbreak of hostilities
in Europe, this foreign supply has been interrupted and constantly
threatened with nearly complete cessation. Until the present date,
German makers have been able to supply a considerable proportion
of the normal demands of their customers, but not entirely. Some
important dyes are totally unobtainable. Prices have mounted from
25 to 50 per cent on such dyestuffs as can be delivered. The imports
may cease any day through inability to make shipments, on account
of maritime dangers, or what is more probable, through the military
necessity of commandeering the available supply of the chief coal-
tar crude material, benzol, for use as a motor fuel, or diverting the
limited supply of nitric acid — the chief chemical used in color manu-
facture — to the manufacture of explosives.
The multitude of users of dyestuffs in the United States have
been crippled in various ways, forced to change designs, or abandon
certain products, or to revert to a temporary use of natural dye-
stuffs, with all the accessory readjustment and revolution in dyeing
processes. On every hand there is difficulty in meeting contract
specifications and in making definite plans and agreements for the
future. The importation of dyewood has quickly increased. It is
now four times as great as in normal times. Prices of these dyewoods
have mounted. Fustic, for example, has doubled in price.
The four American establishments making artificial dyestuffs have
done their best to meet the emergency by enlarging the ordinary
output. They have been crippled by the difficulties or impossibility
of securing half-manufactured materials from abroad or crude ma-
terials at home. Some large consumers of dyestuffs have erected
emergency plants and make the colors they absolutely need, but at
DOMINANCE OF THE GERMAN INDUSTRY.
In all this annoyance, loss, and uncertainty why do we not have an
American coal-tar chemical industry, capable of meeting the Nation's
demands, self-contained and independent of foreign control, utiliz-
ing our native raw material?
A careful analysis of the situation shows that not only is the
American * supply and the limited American production of coal-tar
dyestuffs completely dominated by the German industry, but that
this is the case throughout the world. Even countries such as
Great Britain and France, with ample supplies of crude material and
highly developed industrial power, are in the same condition as the
In 1913 the total consumption of artificial dyestuffs in the world
had attained a value of over $92,000,000. Germany furnished 74
per cent of the entire amount and over one-half of the materials
needed to make the remainder. The only country, in addition to
Germany, manufacturing dyestuffs in any noteworthy manner for
the world's markets is Switzerland. That country relies, however,
for its crude and half-manufactured materials chiefly upon German
sources. The dominance of Germany in the dyestuff production and
DYESTUFFS FOli AMFHTCAN ENDUSTRIES. 9
commerce of the entire world is so marked, and inherently of such
potential might, that it docs not hesitate to make itself felt when-
ever and wherever an effort is made toward emancipation from its
control. The methods used are those often associated with the
working of great industrial corporations in various lands and now
effectively cheeked by legal enactment in the United States. In the
case of the German coal-tar chemical industry, the field is intcrna-
tional and its operations are unchecked by law. Its influence has
been felt at once in our own country when efforts to manufacture
intermediate compounds or finished dyes threatened in any way the
interests of the German production and trade.
ADVANTAGES POSSESSED BY GERMAN MANUFACTURERS.
The coal-tar chemical industry includes not only the manufacture
of dyestuffs, but of a number of valuable medicinal preparations, and
of various high explosives. It is based upon the use of crude com-
pounds present to a small extent in the tar obtained in the de-
structive distillation of coal in gas works and coke ovens. These
10 crude compounds — benzol, carbolic acid, anthracene, etc. — are
separated from some 145 other substances present in tar, by frac-
tional distillation. This is the work of the tar distiller. From the 10
crudes, nearly 300 more complex compounds, none of them dyes,
are produced by highly refined and complicated chemical and me-
chanical processes, involving in most cases a number of complete
chemical transformations. These serve as the materials for the
manufacture of about 920 dyestuffs now in current use.
In the case of Germany, the domestic supply of ' ' crudes ' ' is amply
sufficient. The color factories make all of the 300 intermediates re-
quired for Germany's own industry and a large share of those used
in the very restricted production of other lands.
The industry has been chiefly developed by the inventive power
of German chemists, combined with a wealth of technical skill and
keen business management, scarcely equaled in the history of any
other branch of manufacture. The 21 German companies engaged
in the dyestuff manufacture have a nommal capital of over
$36,700,000 on which dividends average 22 per cent. Actual profits
often reach 50 per cent. The great excesses have been devoted to
new construction. It is the most remunerative industry in the
Empire, the one most solidly and formidably intrenched, the one of
which the nation is most proud as showing the triumph of science
applied to industrial purposes, and the one illustrating most strik-
ingly the ability to win and maintain international supremacy in a
ABUNDANCE OF AMERICAN RAW MATERIAL.
In the United States the supply of coal tar is ample, sufficient to
provide in abundance all of the crudes required for the manufacture
of the dyestuffs consumed in the country. The amount of valuable
by-products not yet recovered in our present coking plants amounts
to $75,000,000 annually. With adequate provision to save all the
benzol and tar liberated in American coke ovens, enough of the 10
crudes could be secured to more than cover the world's consumption
in making artificial dyestuffs.
10 DYESTUFFS FOR AMERICAN INDUSTRIES.
If a commercial demand is present, American tar works can
quickly provide all of the crudes needed, practically as cheaply as
in Europe. In the manufacture of intermediates the production is
restricted to four or five compounds, and these cover about one-
quarter of the needs of American color works.
Our manufacture of heavy chemicals is well developed, able to
expand rapidly, and supply all needed chemicals for the production
of intermediates and their transformation into finished dyes.
The four establishments devoted to the production of dyes supply
nearly 100 different colors, largely, however, as already stated, by
11 assembling" nearly finished products of foreign origin. These
American firms are bold and enterprising, commanding about
$3,000,000 capital, evidently doing the best they can under existing
conditions to build up a national industry.
Investigation shows that their advance, beyond certain limits,
in the manufacture of either intermediate or finished dyes is per-
sistently checked and prevented by the united action of German
producers in underselling. The entire German color industry is so
completely organized and accustomed to act as a unit in furthering
the general interests, at home and abroad, that little success in facing
their determined opposition has heretofore been obtained.
The present crisis has evoked deep interest on the part of all con-
cerned—tar distillers, manufacturers of chemicals, manufacturers
of dyestuffs, the many users of the same, and American economists
in general — as to how the problem can be settled. There is no ques-
tion but that our coke interests are ready to multiply their recovery
plants for the production of benzol and tar, if a permanent market is
assured. There is no question of the readiness of tar distillers to
enlarge their plants for the production of an ample supply of the
needed crudes if a continued demand is certain. American chemical
works and American manufacturers of dyestuffs are ready to embark
capital and experience in building up a distinctly American coal-tar
chemical industry, using entirely American crudes and intermedi-
ates, provided there is adequate legislative prohibition against both
" dumping" or unfair restraint of American trade by the arbitrary
action of foreign monopoly permitted by foreign law and not as yet
forbidden by our own. Domestic makers assert their ability to
make at once over 90 per cent of the dyes now consumed in the
United States, which are now patent-free, and state that the remain-
ing tenth will soon be freed from patent restriction.
WHAT THE AMERICAN INDUSTRY REQUIRES.
There seems to be a consensus of opinion that any rapid develop-
ment and evolution of the dyestuff branch, on a scale commensurate
with the Nation's needs, present and prospective, can be assured only
on the basis of an effective law preventing that action toward con-
trol of our markets by a foreign monopoly which is now prohibited
to a domestic monopoly. Some of the largest manufacturers have
personally informed the department that what is needed is not a
tariff change, but laws placing a foreign monopoly on the same basis
as an American one.
American economists feel that the present crisis offers the most
favorable moment to decide upon a policy with regard to this one
DYBSTUFFS FOB AMERICAN [NDUSTBIES. 11
important industry, whether it is to be firmly rooted in American
soil or whether the dependence noon a foreign source is to continue
indefinitely. It is pointed out that each year elapsing increases in
geometrical ratio the difficulties attendant upon any attempt to create
a self-contained American dyestuff industry. Further, it is claimed
that it is tlio oidy highly organized industry not yet brought on a
broad and generous scale within the cycle of American economic
In England and France the textde and other branches have
insisted that the national industries must be permanently freed from
dependence upon a foreign source for one of the vital needs of the
most varied manufactures. Within a fortnight the group of French
chemists intrusted with the problem claim that they have satisfac-
torily solved all difficulties m the way. During the same period
the necessary steps have been taken in England, where the Govern-
ment has provided for the organization of a national company to
create an independent dyestuff industry, contributing nearly
$2,000,000 to its capital, and granting at the same time $500,000 for
the requisite research laboratory.
DYESTUFF SITUATION IN THE UNITED STATES.
There is a large and steadily growing consumption of dyestufls in
the United States required in a variety of industries. The most
important of these industries are: Textiles — cotton, silk, woolen, etc.;
paints and pigments; varnishes; inks; leather articles; feathers.
A great variety of industries, in addition, are closely dependent
upon the above for all that concerns color effects. Prominent among
these are the printing trades; automobile and carriage manufacture;
implement manufacture; paper trade; soap trade; upholstery trade;
millinery, dressmaking, etc.
Further, a notable and increasing number of preparations made
from by-products and accessory products of the manufacture of
artificial dyestuffs are now used in photography, medicine, the pro-
duction of high explosives, and the manufacture of artificial per-
fumes. Economically these are very closely interlocked with the
dyes tuff industry.
Directly and indirectly, a large proportion of American industries
are dependent upon a constant and varied supply of dyestuffs.
DYESTUFFS USED IN THE UNITED STATES.
The dyestuffs consumed by American industries fall into three
classes: Natural organic dyes, mineral dyes, and artificial organic
Until about 1860 the dyeing trades were restricted to the use of
preparations falling in the first two classes. Soon after that date the
earlier aniline colors were introduced into general use. The number
and variety of these artificial products, made from the different con-
stituents of coal tar, rapidly increased. It was soon possible to
replace, in most cases with very pronounced advantages, every tint
and shade yielded by natural and mineral dyes, and, in addition, to
increase greatly the hues available for color designs in a multitude
of industries. The use of the older dyeing materials, both organic
and mineral, quickly lessened. To-day, and for some years past,
the great bulk of the dyestuffs consumed in the United States con-
sists of synthetic products of the coal-tar chemical industry. The
dyestuffs of an earlier day have been in most cases almost completely
superseded. In a few instances they play a minor and humble role,
chiefly as accessories in the use of the artificial dyes.
NATURAL ORGANIC DYES.
The natural organic dyes are conveniently classified in four sub-
divisions: (1) Indigo; (2) logwood; (3) red dyes; (4) yellow dyes.
(1) Indigo. — This substance, obtained from various plants of the
genus Indigofera, was for centuries the most important of all dyestuffs.
Until quite recently it was supplied from Asiatic countries, chiefly
from India, and to some extent from tropical America. The natural
dyestuff is now replaced almost entirely by the synthetic product,
which has manifest advantages in uniformity of strength and shade,
as well as in price. The amount of natural indigo now used in the
United States is about 7 per cent of the total amount of indigo.
DYESTUFFS FOR AMERICAN INDUSTRIES. 13
(2) Logwood. — This dye is extracted from campeachy wood, found
in tropical and subtropical America. Our supply comes almost
entirely from Jamaica. The extraction of the coloring matter from
the wood is done usually in American mills, although a certain
amount of extract is also imported. Next to indigo, logwood was,
until the past half century, the most important dyes tuff known. It
was universally employed for the dyeing of black on all classes of
fabrics, as was indigo for the production of blue. It is to-day the
only natural coloring matter, except indigo, employed extensively
by the dyer. While of limited application now on cotton and wool,
for the production of very cheap blacks, there is still a large amount
used in dyeing silk, to the fiber of which it gives greater opacity than
can be obtained from coal-tar dyes. There is also an extended use
in dyeing leather. Considerable amounts are employed in connection
with dyes tuffs, in order to tone slightly the shade produced.
(3) Red dyes. — These include among the dyewoods, Brazil wood,
peach wood, Japan wood, and Lima wood, which yield soluble
tinctorial matters; and barwood, camwood, and Saunders wood,
which contain insoluble coloring substances. None of these to-day
has more than a very limited use. Most of the woods in question
are supplied by Central America and South America.
Madder, obtained from the root of the Rubia tinctoria, used for
centuries to produce the famous " Turkey red," has now almost dis-
appeared from commerce. Its coloring principle, alizarin, has been
manufactured synthetically from the anthracene of coal tar since
1871. A small amount of the root is still imported.
Cochineal, a brilliant scarlet, extracted from the female of the
insect Coccus cacti, found abundantly on the cactus plant in Mexico
and Central America, was once a valued dye for woolens, and is still
employed to dye the uniforms of the British army. It resisted
longer than madder the invasion of artificial dyestuffs, but its use
in the United States is now very limited.
Orchil and its dried extract, cudbear, found very extensive use
in producing purplish-red and reddish-brown shades on wool and on
silk. It is extracted from lichens, found in abundance on the sea-
coasts of subtropical countries. Lower California formerly yielded
great quantities. At present the use is restricted and limited chiefly
to toning the effects produced by other dyes.
Annatto, from the fruit of the Bixa orellana, in South America,
has a limited application in silk dyeing. It is more largely used to
Safflower, the dried florets of Carthamus tinctorius, has a very
slight use for imparting pinks to cheap cottons.
(4) Yellow dyes. — The principal yellow dye is fustic, obtained from
the wood of Morus tinctoria, a tree occurring abundantly in the
West Indies and Central and South America. Formerly used largely
for yellows and olives, it now finds a limited employment for toning
logwood effects, especially on woolens.
Quercitron, extracted from a species of oak in the Middle and
Southern States, still has a limited use in calico printing.
Persian berries, the unripe berries of the buckthorn, imported
from the Orient, are also used to a slight extent for calico printing.
Turmeric, extracted from Curcuma tinctoria, an Asiatic root, has
a very restricted use, chiefly in producing composite shades.
DYESTUFFS FOE AMERICAN INDUSTRIES.
Cutch, obtained from an Indian variety of acacia, is employed
slightly for a few brown shades, but more extensively as a tannin
mordant on cottons.
The displacement of these natural dyes by artificial colors was not
due entirely to the fact that the latter could often be manufactured
more cheaply. Most of the vegetable dyes were far removed from
being pure dyes tuffs. The extracts obtained from woods and plants
contained, in addition, a variety of non-tinctorial substances, resins,
tannins, sugars, pectinous bodies, etc. It was practically impossible
to isolate the pure coloring matter. As a consequence, the extracts
varied seriously in their strength, and the colors imparted were dull.
The processes of dyeing became easier, simpler, and cheaper, and
could be readily standardized. It was further possible to extend
greatly the range of colors. Many tones and shades, hitherto un-
known, were at the service of the dyer. Most important of all was
the fact that the artificial dyestuffs, as a rule, were fast as compared
with most of the natural colors. Indigo was the fastest color, and
still represents the standard for comparison. Madder was practically
as fast, but neither could be obtained from their vegetable sources in
a form at all pure or approaching uniformity. The synthetic prod-
ucts were pure and of uniform strength. Cochineal was a fairly fast
color, faster than the earlier coal-tar scarlets; and although the latter
were cheaper, the animal dyes tuff held its own until the appearance
of anthracene and chrome scarlets, which possessed even higher de-
grees of permanence.
The other natural dyestuffs enumerated above were highly fugitive,
as compared with the corresponding coal-tar colors, which appeared
in rapid succession from 1860 on. Logwood was fast to washing, but
not very resistant to light or on exposure to weather. It held its
own, however, until the appearance of the fast alizarin blacks. Even
now it is employed largely for cheap grades of cotton and woolen,
and is the one natural dyestuff that continues to maintain a rela-
tively important position in the dyeing branch.
AVith regard to the sources of the natural organic dyestuffs, it will
be noticed that the present supply of the United States is chiefly
drawn from the tropical and subtropical regions of the Western
Hemisphere. A few materials — natural indigo, cutch, Persian berries,
madder, and turmeric — come from Asia. A single dyestuff, quercit-
ron, is indigenous to the United States.
IMPORTATION OF NATURAL ORGANIC DYES.
The following table gives the quantity and value of the imports of
natural organic dyestuffs into the United States for the fiscal year
ending June 30, 1913:
Annatto pounds. .
Madder, ground pounds. .
Madder, extract do
Cochineal pounds. .
Persian berries,extract pounds. .
Indigo, natural pounds. .
Logwood tons. .
Logwood (and other wood) ex-
DYESTUFFS FOR AMERICAN INDUSTRIES. 15
The use of inorganic coloring materials for the production of dyeing
effects by direct precipitatioD in the fibers of textiles was formerly of
considerable Importance. Most, of the processes once in vogue are
now completely obsolete 4 . The few still in occasional use arc of minor
value and limited application. They are comprised in the following
Chrome yellow and orange. — These are dependent upon the use of
lead acetate and potassium bichromate.
Iron bujf. — Obtained by the precipitation of ferric hydroxide from
soluble iron salts.
Iron gray. — Obtained by the precipitation of tannate of iron from
Manganese brown. — Precipitation of manganic oxide from soluble
Chrome green. — Obtained by the use of chrome alum. In combi-
nation with iron buff this is now employed to some extent to produce
the popular khaki effects.
Prussian blue. — Obtained by the use of potassium ferrocyanide
and soluble iron salts. There is a somewhat extended use, in connec-
tion with other coloring materials, for the dyeing of silk.
Most of the mineral dyestuffs enumerated above are currently
manufactured in the United States. Manganese compounds are,
however, usually imported from Europe, and potassium ferrocyanide
is chiefly of foreign origin. In 1913 the import of this salt from
Europe reached a value of $309,000.
ARTIFICIAL ORGANIC DYES.
The great volume of the dyestuffs consumed by American indus-
tries to-day consists of organic compounds, usually of very complex
composition, the raw materials for which are found in the products
of the destructive distillation of coal, as carried on in the retorts
of gas works or ovens for manufacturing coke. As already men-
tioned, the first of these artificial dyestuffs appeared a little over
half a century ago, and rapidly, one after another, the natural
organic dyes and the mineral dyes were displaced from their posi-
tions and reduced to minor and subordinate rank, if not forced to dis-
appear completely from use.
The consumption of the artificial coal-tar colors in the United
States has now assumed large dimensions. The increase in this
consumption keeps even pace with the growth of American manu-
facturing industries, and more especially with the development of
the various textile branches.
It has been of far-reaching influence in determining the expansion
of cotton manufacture. While wool and silk were dyed with com-
parative facility by vegetable dyes, the contrary was the case with
cotton wares. The inert character of the cotton fiber toward tinc-
torial substances, and the difficulty of mordanting it with metallic
salts, caused a serious limitation in the range of colors and processes
available for dyeing cotton materials, and greatly restricted their use.
The discovery of aniline dyes, capable of dyeing cotton directly,
was a notable step forward, despite the fact that these earlier prod-
86201°— 15 2
16 DYESTUFFS FOE AMERICAN INDUSTRIES.
ucts were not very fast, and could not be employed on fabrics requir-
ing much laundering. The later discovery of the fast vat dyes of
the indigo class removed this restriction on the use of colored cotton
goods. To-day cotton can be dyed in every variety' of tint, and
the colors are practically fast, as permanent as the fiber itself. This
has led to an enormous development in cotton manufacture, and the
products are employed more and more extensively in household
economy and for wearing apparel.
The great bulk of the artificial dyes is, however, used on woolen
fabrics. These can not be washed frequently without suffering from
shrinkage and in other ways. Hence, if intended for articles of
apparel and the like, they are almost always dyed, and usually in
rather dark colors. This means large quantities of dyestuff. The
same rule applies to the vast amounts of woolen material absorbed
by the carpet, rug, and upholstery industries. Such wares require a
great consumption of acid dyes, indigo, and the alizarin colors, with
smaller amounts of the other fast vat dyes. Most of the latter,
involving application in strongly alkaline solutions, are in conse-
quence not adapted for use on wool fibers.
The great diversity of the modern demands for colored textiles,
paper, and the like, has called for equal diversity in the dyestuffs
employed, not only as regards color, but also as regards fastness to
light or washing.
At present the American demand calls for over 900 different arti-
ficial dyestuffs. A small group includes colors used in very large
amounts. In another much more numerous group fall colors em-
ployed in moderate but still noteworthy quantities. The majority
of the dyes enumerated in current price fists are demanded in small
amounts and for special purposes or qualities. This third category
includes most of the very high-priced dyestuffs. The necessity of
providing the great variety of colors found in this category is a
dominant factor in the dyestuff industry.
DOMESTIC MANUFACTURE OF ARTIFICIAL DYESTUFFS.
The demand for artificial dyes in the United States is met to some
extent by the domestic coal-tar dye industry. The great bulk of
dyes used, however, is imported from Europe, Germany being the
It is not easy to estimate the value of the current annual produc-
tion in the United States of coal-tar dyestuffs. Estimates furnished
by those engaged in the manufacture range from $2,000,000 to
$5,000,000. The census report of 1909 gives $3,462,000 as the
value of artificial dyestuffs produced in that year. Among our
exports of domestic manufacture there has been for five years an
average export of "dyes and dyestuffs' 7 amounting to $345,000. It
is doubtful whether artificial dyestuffs constitute any appreciable
share of this item, a large portion of which goes to Canada. It is
probable that the American consumption of artificial dyes of do-
mestic origin does not vary much from $3,000,000 per annum.
The returns of our foreign commerce for the fiscal years ending
June 30, 1909-1914, give the following values for the imports into
the United States of coal-tar dyestuffs:
DYBSTUFFS FOB AMERICAN [NDTJSTRIES.
Alizarin and alizarin dyes
Other coal-tar dyes
6, 022,'. 186
1,01 l, 181
Alizarin and indigo and their derivatives are imported duty free.
Other artificial dyes'pay a duty of 30 per cent. The figures for indigo
do not include natural indigo from Asia, and from British ports.
The annual value of the imports of natural indigo has sunk from
si.-)S,000 in 1909 to $78,000 in 1914. Coal-tar dyes paid in 1913
duties amounting to $2,071,000 and in 1914 to $2,261,361. There
is a small export, chiefly to Canada, of foreign-made artificial dyes.
Its value in 1913 was $46,249, and in 1914 $38,257.
The German official statistics for the calendar year 1913 give the
export of dyes to the United States as $9,030,000, and the imports
of such wares from the United States as $12,000.
The average annual value of the imports of coal-tar dyes during
the last three years was $8,781,736. This is the cost price abroad.
With added amounts paid for duties, about $2,000,000, and expenses
and profits, the sum annually expended for foreign coal-tar dyes
exceeds $12,000,000. Assuming the value of the colors manufac-
tured and employed in the United States to be approximately
$3,000,000, it is found that xAmerican consumers are now paying
annually about $15,000,000 for coal-tar dyes.
FOKEIGN SOURCES OF ARTIFICIAL DYESTUFFS.
If the general imports of coal-tar dyes into the United States are
analyzed as to country of origin, the following is found to be the
case for the imports of 1913: Of alizarin and derivatives, Germany
supplies 99 per cent; of synthetic indigo, Germany supplies 96 per
cent, and Switzerland, 2.4 per cent; of other coal-tar dyes, Germany
supplies 81 per cent, Switzerland 12 per cent, the United Kingdom
2.8 per cent, Belgium 2.5 per cent, and France 1.0 per cent.
The import from Belgium is supposed to be largely of German
origin. The total value of the German import in 1913 was $8,538,000.
It constituted 86 per cent of the value of imported artificial dyestuffk
The Swiss import reached $918,232. It formed 9 per cent of the
total value. It will be seen that, apart from the modest contribution
of Switzerland, the United States depends almost entirely on Ger-
many for its supply of imported artificial dyestuffs.
ECONOMIC EFFECTS OF DEPENDENCE UPON A SINGLE FOREIGN SOURCE.
The economic dependence of the United States, and in fact of all
nations, upon a single foreign source for the regular supply of an
important class of manufactures is comparable in many respects to
the general dependence upon Chile for saltpeter, upon Russia for
platinum, and upon Germany for potash, all three being natural
18 DYESTUFFS FOE AMERICAN INDUSTRIES.
The danger inherent to such a state of dependence has been sharply
brought to view in the world-wide experience of the last seven months.
Some countries have been deprived almost entirely of their customary
supplies of artificial dyes. In others, notably in our own land, the
supply has been intermittent and its continuance uncertain.
Thousands of American industrial plants and an army of opera-
tives, with their dependents, have been threatened with a serious
arrest of manufacturing activities. In many cases it has been im-
possible to fill contracts; in a multitude of instances managers of
large establishments have had to grapple seriously with the problem
of how to continue manufacture with limited supplies or with no
supplies of the customary coloring matters.
Fortunately, after the first excitement following the outbreak of hos-
tilities, in August, 1914, and the interruption for some weeks of all
shipments of foreign dyestuffs, means were found to resume the ex-
portation from Germany and Switzerland. By the close of 1914 most
American manufacturers had been supplied with the majority of their
customary supplies of coal-tar dyes in nearly normal amount.
On August 1, 1914, the textile works had supplies adequate for the
needs of their mills for two or three months. The German Govern-
ment granted permission for the monthly export to the United States,
in American vessels, of a maximum allowance of 2,300 tons of artificial
The result has been that, while a few cases of hardship were una-
voidable, and here and there changes in style, etc., were required,
textile branches have not materially suffered thus far.
INCREASED COST OF COAL-TAR DYES.
There has been an increase in the cost of dyes, naturally inevitable
with the rise in freight rates and insurance. In September, 1914,
the average increase on foreign dyes was estimated at about 25 per
cent. Since then there has been a rise of about the same amount.
The price of alizarin is now about 50 per cent above that of August,
1914. In some instances very abnormal rates are quoted. Ben-
zopurpurin, an important cotton dye, selling ordinarily at 14 cents
per pound, is now (Mar. 15) quoted at 80 cents.
American manufacturers of dyes have been able to retain old
rates on about one-third of their products, while the prices of the
rest have doubled in consequence of the increased cost of raw mate-
rial. In general, there has been a pleasant concurrence of opinion
on the part of American consumers of dyestuffs that the few American
manufacturers in this branch have taken no undue advantage of the
critical situation, and, further, that the resident agents of foreign
makers have shown great resolution and energy in seeking to secure
supplies for their regular customers and in distributing equitably
such as have been received.
OUTLOOK FOR THE IMMEDIATE FUTURE.
While nearly enough coal-tar dyes are now being shipped from
Germany to meet the current needs of American consumers, the
fact is not disguised on either side of the ocean that at any moment
this supply may be largely or totally suspended. Several factors
enter here into consideration. Naval operations in the existing war
DYESTUFFS FOB AMERICAN [NDUSTRIES. 19
may assume such a character that maritime connections with the
port of Rotterdam may be completely severed. There is in this case
a possibility of utilizing an Italian port, such as Genoa, from which
small amounts of dyes haw already been shipped to Now York.
The Gorman supply of benzol may be commandeered for use in
mot tus in place of gasoline. Benzol is the raw material absolutely
essential for the manufacture of the majority of aniline dyes.
The German Government may require for military purposes, in the
manufacture of explosives, the entire available stock of nitric acid.
'Phis would be practically equivalent to closing nearly every factory
engaged in making dyestuffs. There is hardly a dye made, except
alizarin, in the manufacture of which nitric acid is not required.
Some classes of dyestuffs may be crippled in their manufacture by
the lack of an important raw material. Carbolic acid is used in large
amounts for the manufacture of explosives. It is also indispen-
sable for the production of a variety of dyes.
It is thus evident that any prolongation of the existing war increases
the probabilities of a serious famine in artificial dyestuffs.
ALTERNATIVES IN CASE OF A DYESTUFF FAMINE.
Responsible heads of textile works who have studied the problem
find three outlets from the dilemma:
(1) The textile industries may be forced to put upon the market,
to a large extent, goods that are undyed. This would be an unsatis-
factory solution. The demand for such goods would certainly fall
below the normal, and there would be a serious drop in prices.
(2) A return may be made temporarily to the use of natural dye-
stuffs. In some instances vegetable substitutes can be obtained with
tolerable rapidity. This would be particularly the case with logwood.
The output can be quickly increased and provision made for dyeing
black on both cottons and woolens, although at the sacrifice of fast-
ness. Fairly ample supplies of orchil can be secured at short notice
and can be used for reds and browns in dyeing carpets and woolens
generally. There would also be no great delay in obtaining a stock
of yellow woods. Considerable time would be lost, however, before
the coloring matters could be extracted and properly treated in order
to develop desired strength and quality. In the case of indigo and
madder several years would elapse before the needed stocks could be
obtained. It would be scarcely possible to collect more than a frac-
tion of the cochineal required for scarlets. The majority of tints
now in common use could not be produced at all. Needless to say,
there would be involved a revolution in the methods of dyeing.
(3) The attempt could be made to build up rapidly an American
coal-tar dyestuff industry, self-contained and independent, based
upon the use of American raw materials, and providing American
consumers with all needed artificial dyestuffs. This would certainly
demand some time, but would insure permanent freedom in the future
from the dangers to which so many of our great industries are now
The desirability, and even urgency, of adopting the necessary
measures for the creation of such a national industry have been ad-
vocated most earnestly by consumers of dyestuffs, by chemists, and
20 DYESTUFFS FOR AMERICAN INDUSTRIES.
It seems proper here to consider why such a complete industry has
not yet been established in the United States, and under what con-
ditions it can be called into existence. This involves a study of the
existing coal-tar chemical industry in the United States, its limita-
tions, and its successes, and a study of the German coal-tar industry,
with the explanation of its present technical and commercial domi-
nation in the world's trade.
OUTLINE OF THE COAL-TAR CHEMICAL INDUSTRY.
When coal undergoes destructive distillation in coke ovens or gas
retorts, the average products are as follows: Coke, 72 per cent; gas,
22 per cent; tar, 6 per cent.
The tar contains some 155 different chemical compounds, none of
which are dyes. Ten of these substances are utilized in the manu-
facture of dyestuffs. They are: Benzol, toluol, xylol, phenol, cresol,
naphthalene, anthracene, methyl anthracene, phenanthrene, and car-
bazol. The first three are present to a considerable extent in the
crude gas, given off on distillation. Only by the use of specially
designed purifiers can they be removed or separated.
The 10 substances enumerated form 6 to 12 per cent of the coal
tar, the amounts varying according to the character of distillation.
The average yield is about as follows:
Substances, age of age of
Benzol, toluol, xylol 1. 75 0. 115
Phenol, cresol .25 . 015
Naphthalene 5. 95 .357
Anthracene and remaining compounds .20 . 012
These 10 primary, or crude, coal-tar products are separated from
one another, and from the great variety of carbon compounds accom-
panying them in the tar, by fractional distillation. This operation
is carried on in the tar distilleries, which supply likewise pitch, creo-
sote oil, naphtha, and other crude mixtures of coal-tar constituents.
From the 10 primary " crudes," chemical works of a high charac-
ter prepare nearly 300 so-called "intermediates," compounds that
are not dyes, but which are susceptible by direct reactions of being
transformed into coloring matters. A number of these intermediates
serve also in the manufacture of medicinal preparations, photo-
graphic chemicals, etc. Leading intermediates are aniline oil and
salts, pure aniline and toluidine, nitrobenzol, naphthol, phthalic acid,
salicylic acid, resorcin, anthraquinone, etc. These intermediate
products serve as the raw material for the manufacturer of dyes.
From them he makes over 900 different dyestuffs now currently
sold in the world's markets.
In a general way it may be stated that the average intermediate
sells for five times as much as the average crude coal-tar derivative,
and the average finished dye for ten times as much, a very material
enhancement in value.
The number of intermediates now in active use does not exhaust
the possibilities in this class. Many hundred more are known to the
chemist and can be employed in dye manufacture. Less than 300
nvKSTrn-'s i'oi; am kkkwx i n mistimes. 21
have been found sufficient fco meet the needs of makers and to com-
bine technical with economic advantages.
The same may be said of finished dyes. The number of possible
distinct dyestuffs covered by patent specifications up to the present
would run into the millions. Of the many possibilities only 900 have.
won a recognized position, and of (hose only 400 are of very extended
It is doubtful whether many additions of value will be made to the
current list of artificial dyestuffs in the immediate future. The field
has been worked most thoroughly by color chemists. During the
past decade oidy a single new class of dyes has been discovered and
placed on the market.
Briefly summarizing the coal-tar clyestuff industry, the following
features are obviously essential to success:
The presence of an ample supply of coal.
The extensive use of this coal for gas and coke manufacture.
The use of a plant that allows the recovery of the volatile organic compounds formed
during destructive distillation.
The industrial treatment of the tar produced, so as to separate and furnish in a
fairly pure form 10 crude substances.
The existence of well-equipped chemical works, able to transform the 10 crudes
into nearly 300 more complex intermediate compounds.
The existence of highly organized works for manufacturing from these intermediates
some 900 different dyestuffs.
An ample and sine supply of a variety of acids and heavy chemicals for effecting
the numerous transformations.
A relatively large number of chemists who have enjoyed university training.
COAL-TAR DYE INDUSTRY IN THE UNITED STATES.
Considering the natural resources and economic conditions of the
United States, it could reasonably be expected that a well-developed
coal-tar chemical industry would nourish here.
The coal supply is abundant. The unmined coal deposits are five
times greater than the reserves of Europe. Large amounts of coal
are used in furnishing an illuminant and fuel for a population of
100,000,000. Still larger amounts are consumed in providing coke
for the enormous iron and steel industry.
The consumption of artificial dyestuffs is large — about $15,000,000
in value annually, as already noted.
The many universities and schools of science are furnishing yearly
a considerable number of w^ell-equipped young chemists.
Nearly all of the world's great industries are encountered in the
United States, finery developed, wdth high standards of efficiency.
And yet, despite these favoring conditions, the production of arti-
ficial dyestuffs in the United States is hardly half of that manufactured
in Switzerland, a small country without a coal mine.
SLOW x DEVELOPMENT OF THE AMERICAN INDUSTRY.
The first aniline dye, mauve, was discovered by Perkins, in England,
in 1856. It was followed in the same year by magenta and fuchsine,
and the manufacture began in England on a small and not very re-
munerative scale. Little progress was made until the appearance, in
1862, of the soluble blues. Then followed in 1863, Hoffman's violet
and Bismarck brown; in 1864, naphthol yellow; in 1867, the nigro-
22 DYESTUFFS FOB AMERICAN INDUSTRIES.
The manufacture was taken up with great energy in both Germany
and Switzerland. A vast amount of patient, intelligent, and careful
research was expended upon the new field. The industry was started
in France and England, but with less zeal and scientific research.
In 1871 artificial alizarin appeared, and a few years later saw the
discovery of chrysoidine, malachite green, eosine, and a number of the
current standard dyes. The manufacture was growing rapidly in
Germany and becoming well intrenched.
During this period the consumption of aniline dyes assumed large
proportions in the United State, which became the leading customer
of the German factories.
There seemed a good opening for American enterprise, and in 1879
the first establishment for the manufacture of artificial dyestuffs was
started at Buffalo. Eight others were opened soon after. At that
time the manufacture was based upon the use of the intermediates
imported from Europe. It was difficult to obtain an adequate supply
of benzol from domestic tar works. The Buffalo works did, for a few
years beginning with 1884, make its own aniline oil, but was forced
to abandon the attempt on account of the uncertainty of obtaining
the raw material.
The industry was exceedingly remunerative at the outset. There
seemed to be a good prospect of soon becoming independent of other
nations in this branch, except so far as patent protection existed,
although for the time being the industry was based upon the use of
intermediates of foreign origin, procured from Germany and Great
In 1883, however, the growth of the industry was suddenly checked.
Within a year five of the nine establishments were forced to close.
The other four continued to manufacture on a close margin. These
four having been carefully conducted, have gradually developed and
now seem to be flourishing. The capital invested is estimated at
$2,000,000 to $3,000,000 and the annual output is about $3,000,000.
There is not much competition between the different firms, each spe-
cializing to some extent, one for woolen dyes, another for cotton,
another for paper, etc. All have to meet keen competition on the
part of the representatives of German manufacturing firms, and the
claim is made that they have to contend with underselling. Three of
these establishments are in the vicinity of New York. The oldest and
largest is still located in Buffalo. It has shown a commendable
degree of enterprise, having taken out 16 patents for new colors and
intermediate products. Two of its patented products are manufac-
tured extensively in Germany under license.
These firms have employed intermediates, mostly from Germany,
as the basis of their manufacture. The works at Buffalo have,
however, as already mentioned, made aniline oil on a large scale,
and have also demonstrated their ability to manufacture in tech-
nically pure form quite a group of intermediates, such as nitrobenzol,
dinitrobenzol, nitrotoluol, dinitrotoluol, dimethylaniline, and a va-
riety of sulphoacids. Pure phenol and pure naphthalene have also
been made in their works. In all cases the production has been
abandoned because German makers reduced their prices on interme-
diates to such an extent that competition became hopeless.
During the last seven months, when it has been almost impossible to
obtain intermediates from Europe, the American works nave hur-
DYESTUFFS FOR AMERICAN INDUSTRIES. 23
riedly put up emergency plants and made the requisite intermediates
at considerable expense in order to avoid a complete stoppage. In
this connection material assistance lias been rendered by the intro-
duction in 1911 of the manufacture of uitrobenzol and aniline oil
and salts in the works of one of the largest American companies en-
gaged in the production of chemicals. This company has been able
to supply about one-quarter of the demand of American dyestuff
manufacturers for the intermediates in question.
The quality of these compounds has been recognized as fully equal
to that of European products, and the ability to make these com-
pounds in the United States from American benzol, so hotly con-
tested on the other side of the ocean, has been abundantly demon-
A plant is now under erection that will be able to provide for one-
half of the needs of the American color makers, as far as aniline oil
and salts are concerned, and will be capable of easy expansion.
The dyes manufactured by the four American establishments are
chiefly standard colors, called for in fairly large quantities, on which
patent rights have expired. They number about 100 and represent
the active types in the trade. No attempt is made to manufacture
synthetic indigo, which remains under patent protection for a few
years longer, or alizarin, which requires an exceedingly expensive
plant. Both of these dyestuffs are on the free list.
Mention should be made of a fifth factory for making coal-tar dyes
which has been established in the State of New York by one of the
largest German firms engaged in the manufacture. This branch
house, according to statements, is occupied with the transformation
of intermediates into finished dyes, especially in such cases where the
series of operations is costly, and the last steps relatively simple and
inexpensive. There is manifestly a temptation to utilize tariff pro-
visions in this manner, and the practice is probably not limited to
the one foreign branch. An unfinished dyestuff pays 10 per cent
duty or no duty, as compared with a duty of 30 per cent on the
finished product. The cost of the last steps in "assembling" the
finished dye, may, however, be less than 1 per cent of its total value.
Reviewing the growth and present status of the manufacture of
artificial dyestuffs in the United States, it may be said that all has
practically been accomplished that could safely be attempted in the
face of exceptionally powerful competition. Those conducting these
industries have shown an abundant measure of perseverance and
patience in facing economic difficulties and gradually building up as
extensive a structure as now exists. There seems to be present a
determination and readiness to invest capital and energy on a large
scale in expanding the industry as soon as the factors of safety are
AMERICAN SUPPLY OF RAW MATERIALS.
As already noted, attempts in the past to manufacture intermediates
have been hampered by the insufficiency of the domestic supply of
coal-tar crudes. It is desirable at this point to know exactly how
far the recovery of the by-products of American gas works and coke
ovens is developed and to what extent they can supply in the im-
mediate future the crudes needed by an expanded coal-tar chemical
industry. The two sources of coal tar are gas works and coke plants.
24 DYESTTJFFS FOE AMERICAN INDUSTRIES.
COAL TAR FROM GAS WORKS.
In 1909, according to the census returns, the coal used in American
gas works amounted to 4,941,000 tons, valued at $16,305,000. At
the same time 580,000,000 gallons of oil, valued at $17,346,000, were
employed hi the production of gas. The tar collected was 92,153,000
gallons. Of this quantity 78,340,000 gallons, valued at $1,876,000,
appear to have come into the market. The valuation is a little
over 2 cents per gallon. This tar is not rich in the hydrocarbons
benzol, toluol, and xylol, as it is sought to retain as large a volume
as possible of these volatile constituents in the gas, in order to in-
crease the illuminating power. Coal gas usually contains from 0.5
to 1.2 per cent of benzol and its homologues. On an average, when
coal is distilled, 100 pounds of coal yield 1.25 pounds of benzol and
its higher homologues that are present in the gas evolved. Of this
amount 0.94 pound is pure benzol, and 0.31 poimd is toluol and
xylol. A small additional amount is found in the tar. It consists
of 0.05 pound of benzol, and 0.08 pound of toluol and xylol.
The coal tar from gas works contains on an average 0.32 per cent
of pure benzol, 0.50 per cent of toluol and xyol, 0.26 per cent of pure
phenol, 4.5 per cent of pure naphthalene, and 0.44 per cent of pure
Assuming that the present American production of gas tar amounts
to 100,000,000 gallons, this represents about 1,000,000,000 pounds, or
500,000 short tons. From this quantity it is possible, on the above
figures, to extract: Benzol, 1,600 tons; toluol and xylol, 2,500 tons;
phenol, 1,300 tons; naphthalene, 22,500 tons; anthracene, 2,200 tons;
and the minor constituents, cresol, phenanthrene, etc., in proportion.
COAL TAR AND BENZOL FROM COKE WORKS.
The majority of the coke plants in the United States are equipped
with old-fashioned beehive ovens, which allow all gas, ammonia, and
tar to be wasted.
Modern recovery ovens, with condensation plants, have been in-
stalled to some extent in this country. Their use is much more
extended in European coke works, especially in Germany, where
nearly all the by-products are saved. In 1913 there were 102,650
coke ovens in the United States, and of these only 5,688 were retort,
or recovery, ovens. The increase during the year of such ovens was
477. There was a decrease in the number of beehive ovens of 57.
At the close of the year 504 retort ovens were under construction, and
contracts had been made for building many more. During 1913,
30,485 beehive ovens — 31.4 per cent of the entire number — were idle
throughout the entire year.
In 1912 the amount of coal used for coke plants reached 65,578000,
short tons. The coke produced totaled 32,S69,000 tons, valued at
$69,172,000, from beehive ovens, and 11,115,000 tons, valued at
$42,633,000, from recovery ovens; in all, 43,984,000 tons, valued at
$111,805,000. The coke obtained from the recovery ovens repre-
sents 25 per cent of the total product in quantity and 38 per cent in
The retort ovens are expensive, but the increased outlay is more
than compensated by the value of the ammonia, tar, and gas recov-
!)\ KSTUFFS FOR AMERICAN INDUSTRIES. 25
ered, especially if there is an adequate demand al band for the gas.
The recovery plants contain the necessary condensers for collecting
ammonia and tar, bul are not always provided with the "scrubbers,
or benzol towers, designed to extract from the otherwise purified gas
the benzol and toluol present therein and enhancing the value for
In the towers the current of gas comes in contact with the heavier
oils obtained in the distillation of coal tar, and the benzol and toluol
present are largely absorbed by them. The oils, when saturated, are
inn into a still, and the benzol and toluol are driven out by heat and
are collected in suitable condensers. Benzol towers constitute an
important additional item of expense, and introduce an additional
complication into the general process. They give a yield of about
22 pounds of benzol and toluol for each ton of coal submitted to
coking. Their construction has hitherto been largely dependent
upon the current demand for these hydrocarbons. The cost of benzol
towers for a plant coking 300 tons of coal daily is about $21,000 in
Germany. It requires a capital of about $5,000 for operation. The
operating expenses are about $23,000 per annum. Such a plant
gives yearly profits exceeding $30,000 when benzol prices are favor-
able. With low prices for benzol it may barely meet the cost of
operation. The 65,000,000 tons of coal now employed in coking are
capable of producing 715,000 tons of benzol and its homologues from
benzol towers alone, but the cost of the necessary plant would be
It is estimated that our present system of coking involves an annual
loss of $75,000,000, but at the present rate of advance, by 1920 one-
half of our coke supply will come from recovery ovens. The intro-
duction of such ovens in the United States began in 1892.
The tar recovered in American coke plants was 66,300,000 gallons
in 1910. It rose to 94,300,000 gallons in 1912, with a value of
$2,311,000, or 2.45 cents per gallon. The weight of this tar was
about 944,000 tons. Taking as a basis the customary yield obtained
from coke tar, this contains 16,420 tons of benzol, toluol, etc.; 2,380
tons of phenol; 56,600 tons of naphthalene; and 1,890 tons of
anthracene, and the minor constituents in proportion.
From the 65,000,000 tons of coal now used in coking it would,
however, be possible, with complete recovery plants, to obtain
3,350,000 tons of tar, or three and one-half times the present quantit}^.
This would mean a potential supply from the tar of coke plants, on an
existing basis of production, of approximately 58,000 tons of benzol,
toluol, etc.; 8,300 tons of phenol; 200,000 tons of naphthalene; and
6,700 tons of anthracene.
Together, the existing gas and coke production, provided the latter
be completely equipped with recovery plants, can furnish tar and
benzol capable of yielding annually approximately 780,000 tons of
benzol; 9,600 tons of phenol; 222,000 tons of naphthalene; and 9,000
tons of anthracene; and the minor compounds, cresol, methyl, an-
thracene, phenanthrene, and carbazol in the customary relative pro-
From existing American gas works and coke plants, as equipped
at present, about 25,000 tons annually of benzol, toluol, and xylol
can be obtained if there is sufficient demand, and the proportionate
quantities of the other constituents.
26 DYESTUFFS FOR AMERICAN INDUSTRIES.
These figures for the possible and potential production in the
United States of the crude coal-tar products may be compared with
those for the production in Germany.
In 1910 Germany was equipped to produce, if necessary, 98,000
metric tons of benzol and its homologues (metric ton = 2,204.6
pounds). The actual production was 66,000 tons. Of this, 56,000
tons were benzol and 10,000 tons toluol and higher homologues. A
little over one-half of the total product was sold for use in motors,
automobiles, etc. Aniline color works required 32,300 tons. As Ger-
many supplies over two-thirds of the finished coal-tar dyes now pro-
duced, and the great bulk of the intermediates required in other
countries, furnishing from German works nearly all of the crudes, it
is evident that the United States has at hand the raw material requi-
site for supplying the crudes needed in the manufacture of over one-
half the world's supply of artificial dyestuffs. At the same time its
coke industry is capable, upon demand, of furnishing in the future
twenty times as much benzol, etc., as the world now requires for
PRESENT PRODUCTION OF CRUDE TAR PRODUCTS.
The handling of coal tar and its further treatment are concentrated
in a few hands, as is the case in Germany. This has given to the
industry a pronounced unity and economy. Consumers of coal-tar
crudes state that there has been a marked disposition to meet their
needs, and to so adapt and modify manufacturing processes that
domestic demands may be met as far as general market conditions
In 1911 the amount of coal tar subjected to distillation amounted
to 56,000,000 gallons. The remainder of the tar production was
employed in the manufacture of roofing paper and for sprinkling
streets. There is not much attempt to obtain separate products in
a state of purity. The most important products are the light oil,
creosote oil, and the residual pitch. These articles can compete
successfully with European products. The light oil, containing ben-
zol, etc., constitutes about 1 per cent of the tar. It is used largely
for a solvent, for cleaning purposes, and as an illuminant. The
creosote oil constitutes about 23 per cent of the tar and is used exten-
sively for preserving timber. The domestic supply is far from cover-
ing the current demand.
In 1914 the United States imported 61,000,000 gallons of creosote
oil, valued at $3,840,000, Great Britain supplied 41,000,000 gallons,
Germany 10,000,000, and the remainder came largely from Belgium
and the Netherlands. The home production of creosote oil in 1909
was 13,000,000 gallons. It has about doubled since then.
With regard to the production in the United States of the coal-tar
crudes, necessary for dyestuff manufacture, the following is the
Benzol, toluol, xylol. — Such limited amounts as have been called
for to make intermediates in American works, about 500 tons annually,
have been supplied the last few years. Provision can be quickly
made for an ample supply on a much more extensive scale if a per-
manent demand is evident.
DYESTUPPS FOB AMERICAN I NDl 'STKIKS. 27
Phenol, or carbolic acid. — Tho method of treating American coals
is such as to favor a relatively low production of phenol in coal tar.
There has been little attempt to separate, regularly, technically pure
phenol from the tar distillates.
The American demand is covered mostly by importations from
abroad. In 1913 American imports were valued at $675,000. Of
the import of 4,077 tons, Germany supplied 1,354 tons, Great Britain
2,422 tons, and the Netherlands 287 tons. The average price was
$166 per short ton. In addition to furnishing material for a variety
of important dyes, phenol has an extended use in medicine, in the man-
ufacture of explosives, and in various industries. One important
chemical made from phenol is salicylic acid, widely used in medicine
as well as in the manufacture of artificial dyes. This is imported to
the extent of 32,000 pounds. Another derivative is picric acid,
used as an explosive as well as a dye. The import is now 85,000
pounds, valued at $18,000.
The embargo on exports of phenol from Europe during the last few
months, on account of its importance in connection with military
supplies, has forced American chemists to fall back on its synthetic
Eroduction from benzol. The operation is relatively easy. It is
ased upon the transformation of benzol into its sulphonic acid by the
action of sulphuric acid, and the fusion of the product with caustic
soda. With an ample supply of benzol the manufacture of synthetic
phenol in the United States could be readily assured, at a cost not
much in advance of that of the European product.
Naphthalene. — This is a leading constituent of coal tar and fur-
nishes a variety of derivatives employed in dye manufacture. The
bulk of the pure product is used as a moth preventive. The United
States consumes annually about 5,000 short tons. Nearly 1,600 tons
are supplied by American tar distillers. The remainder comes from
Germany and Great Britain, in about equal amounts. Phthalic acid,
one of the most important derivitives of naphthalene, is imported to
the extent of 38 tons annually, with a value of $21,000. Naphtha-
lene is a prominent constituent of the fraction of creosote oil ob-
tained in the distillation of coal tar. It is a purely commercial ques-
tion to the tar distiller, whether he can more profitably sell the crude
creosote oil or separate out the naphthalene present therein.
Anthracene. — This hydrocarbon is also present in the creosote oil,
and the same question arises as to the profit of its separation. No
attempt is made in American tar works to isolate this valuable con-
stituent, which serves as the basis of the manufacture of synthetic
alizarin and all the alizarin dyes tuffs.
The same may be said of the relatively small but still important
amounts of cresol, methylanthracene, phenanthrene, and carbazol,
all of which occur in the creosote oil, and all of which are essential to
an industry providing all current artificial dyestuffs. It should be
mentioned here that the quantity of anthracene present in the coal
tar now treated in American tar works is far in excess of that required
to manufacture the alizarin dyes imported into the United States,
while the naphthalene present could more than meet the demands of
the world's entire dyestuff manufacture.
A competent authority gives the following estimate for products
of the coal-tar industry in the United States for 1914: Total pro-
DYESTUFFS FOE AMERICAN INDUSTRIES.
duction of refined benzol in all forms, 2,550,000 gallons, or about
9,600 short tons (of this amount, 200,000 gallons, or 750 tons, was
devoted to the manufacture of aniline compounds) ; total production
of refined toluol, in all forms, 840,000 gallons, or about 3,200 tons
(nearly all used for making explosives) ; production of refined phenol,
75 tons; production of refined naphthalene, 1,500 tons.
PRICE MOVEMENT OF AMERICAN COAL-TAR CRUDES.
Since August 1, 1914, there has been a steady movement upward
in the market rates for nearly all crude products of coal tar, required
in making dyes tuffs or explosives. The folio whig table shows the
per gallon. .
100 per cent
90 per cent
50 per cent
The present quotation for phenol is nominal. The demand for
phenol is so far in excess of the supply, foreign or domestic, that
exaggerated prices are often offered without finding any taker.
American toluol is used almost entirely for producing high explosives.
The naphthas, mixtures of the hydrocarbons, not used for dyestuffs,
etc., show no tendency to rise.
POSITION OF THE AMERICAN TAR DISTILLER.
The tar industry of the United States is on a different basis from
that of Europe. In Europe its importance is confined almost en-
tirely to the production of raw material for a highly organized
chemical industry. Here the use of tar itself is widespread, while the
utilization of its chief constituent, pitch, is confined to very narrow
limits across the ocean. Pitch forms 70 per cent of coal tar. In
Germany little use is made of it except as a fuel. Nine- tenths of
the pitch supplied by American tar works is employed hi road mak-
ing, in roofing, and in general waterproofing.
The very extended use of creosote oil in the United States makes
it a purely commercial question as to whether the tar distiller should
attempt a refining of its constituents. The current demand in
America for benzol, toluol, and xylol is entirely met by the product
from the benzol towers of coke plants.
To attempt any extended provision for supplying the entire range
of coal-tar crudes, such as might be required in the United States
for the manufacture of its own supply of artificial dyestuffs, would
mean an assurance that the distiller could profitably dispose of
nearly all of the products isolated in a more or less pure form during
DYESTUFFS FOB AMERICAN [NDUSTRIES. 29
the various processes, and secured in far different proportions from
those required in the general manufacture of coal-tar dyestuffs. At
once he would face a very delicate and complicated problem, with
many factors, technical, economic, financial. A dommant factor is
an assured market, if he enlarges his plant on a scale comparable with
Loss than 10 per cent of tar consists of matters available for use in
the dyestuff industry. Jl' a distiller attempts to meet the needs of a
growing or rapidly expanded domestic dyestuff industry, he must
find channels for disposing of the remaining 90 per cent.
The tar distiller feels that he should not be expected to embark in
the manufacture of intermediates, but that this branch should be
undertaken preferably by the producer of heavy chemicals, as the
production of intermediates means a heavy consumption of acids,
alkalies, and a variety of other chemicals.
There seems to be no lack of enterprise in the tar-distilling branch;
but there does seem to be a deep-seated conviction that fundamental
changes in legislation are absolutely essential before any far-reaching
effort can be organized, to assure the preparation from American
coal tar of an adequate supply of " crudes" for the needs of a self-
contained American coal-tar dyestuff industry.
SUPPLY OF GENERAL CHEMICALS REQUIRED.
With regard to the great bulk of the heavy chemicals required in
the coal-tar dyestuff industry, the United States is now compara-
tively independent of the rest of the world. This is especially the
case with sulphuric acid, hydrochloric acid, sodium carbonate,
caustic soda, wood alcohol, grain alcohol, and the chromates, all
of which are used in large amounts. Liquid chlorine can easily be
produced here on a large scale by electrolytic methods if the demand
exists. The same can be said of glacial acetic acid and of acetic
anhydride, the raw material for which is furnished abundantly by
numerous plants for wood distillation. In common with the rest
of the world, the United States depends largely upon Germany for
potash compounds. The world depends likewise upon Chile for the
raw material required in making nitric acid and sodium nitrite,
except as these products are obtained from the air by the new pro-
cesses for oxidizing atmospheric nitrogen. There is promise of this
new industry being created in the United States. For the time being
Norway, with its very cheap water power for generating electricity,
is the only country where the synthetic production of nitric acid is a
pronounced success on a fairly large scale. Most of the nitrite
required for the manufacture of coal-tar dyestuffs is very advan-
tageously manufactured as an adjunct of the Norwegian nitric-acid
production. The bulk of the nitric acid made in Norway is transformed
immediately into nitrates for use as fertilizer. All of Norway's water
power, if utilized for the production of nitric acid and nitrates,
would suffice for the production of only a fraction of the world's
demands. In this connection it is of interest to note that Germany
has hastily erected works on the Rhine for the production of nitric
acid from atmospheric nitrogen, generating the necessary electric
current at high cost by means of coal. The works will be in operation
by April, 1915, and will partly meet the vastly increased demand for
nitric acid required in the manufacture of explosives.
DYESTUFFS FOR AMERICAN INDUSTRIES.
THE GERMAN COAL-TAR DYESTUFF INDUSTRY.
As already noted, all efforts to build up on a large scale a distinctly
American coal-tar chemical industry have been crippled and rendered
useless when brought into conflict with the interests of the German
coal-tar chemical industry. It is necessary to analyze the sources of
this power, exerted apparently with such ease in all the leading indus-
trial countries of the world, but felt most keenly in the United States,
with its abundant supply of the raw materials and its large and rapidly
growing consumption of artificial dyes tuffs.
First of all, it is important to establish just how large a proportion
of the world's production of artificial dyes is made in Germany.
From export returns and careful estimates of local consumption, the
following may be regarded as a fairly approximate statement of the
world's present production of finished coal-tar dyes:
6, 450, 000
92, 150, 000
This shows that Germany furnishes 74 per cent, or about three-
quarters, of the world's dyes.
The production of artificial dyestuffs for exportation is confined
practically to Germany, Great Britain, and Switzerland. The values
of such exports in 1912 were: Germany, $48,430,000, or 88.2 per
cent; Switzerland, $5,450,000, or 9.9 per cent; Great Britain,
$990,000, or 1.8 per cent; total value, $54,870,000. In the world's
markets Germany's domination is evident, Switzerland being prac-
tically the only competitor.
The distribution oi Germany's exports of artificial dyestuffs among
the different countries is a matter of interest. The exports of finished
dyes in 1912 were valued as follows: Aniline dyes, $31,836,000;
alizarin, $2,197,000; anthracene dyes, $3,429,000; indigo, $10,968,000;
total, $48,430,000. The following table, compiled by Dr. Bernhard
C. Hesse, the well-known chemist and statistician, shows very clearly
the present dependence of the various countries upon Germany for
their supplies and the importance of the United States as the leading
customer. Noteworthy is the enormous consumption of synthetic
indigo by China. The table shows the percentage of the exports of
each dye taken by the principal consumers.
DYKSTUFFS KOI! \MKIU('AN \ N Dl'S T1UKS.
/'-/ C< nt.
TRADE IN CRUDES AND INTERMEDIATES.
The domination of the German color industry is, however, greater
than would appear from the export statistics for finished dyes. As
far as the production of crude coal-tar products is concerned, Ger-
many has been for nearly 20 years practically independent of other
countries. Its own tar industry produces, or is capable of producing,
all crude compounds needed in the industry. The nearest approach
to an exception is in the case of anthracene, the raw material for the
manufacture of alizarin and an important class of dyes. There is
enough of this hydrocarbon in German tar to meet the needs of the
dyestufT works. In England, however, the separation of anthracene
from the heavy oil of the tar works has been highly perfected and it
is commercially profitable to draw upon the English supply. The
independence otherwise of the German production of crudes, and its
ability to send supplies to other countries, is shown by the following
summary, for 1912, of Germany's trade in crude coal-tar products:
Benzol and bomologues
2, 778, 000
86201°— 15 3
32 DYESTUFFS FOE AMERICAN INDUSTRIES.
Germany's excess of exports is $1,474,000.
Much more striking and of far-reaching importance is the revela-
tion of the figures contained in the summary, for 1912, of Germany's
trade in intermediate coal-tar products :
Naphthol, and naphthalene compounds
Nitrobenzol, resorcin, phthalic acid, anthraquinone, etc
3, 674, 000
Here is an excess of $3,522,000 in favor of the exports. A calcu-
lation based upon the unit prices of the various coal-tar products
shows that in a rough approximate way crudes worth $1 produce
intermediates worth $3.56 and finished dyes wor.th $7.61. Assum-
ing that one-half of the excess of exports of crudes and all of the
excess of intermediates are used to produce colors in other coun-
tries, the value of the dyes manufactured abroad from German
products would be, from crudes, $5,608,000; from intermediates,
$7,529,000; total, $13,137,000.
These figures show how largely the manufacture of dyes outside
of Germany depends upon the industries of that Empire for the
primary and intermediate compounds serving as raw materials.
The manufacture of artificial dyestuffs outside of Germany has
a value of about $24,000,000, and over one-half is made with mate-
rials from German factories.
The effects of this condition are seen in the trade statistics of
other countries. Switzerland's net excess of crudes imported is
$315,000; of intermediates, $846,000. Austria exports a net excess
of 3,309 metric tons of crudes, and the net excess of imported inter-
mediates is 1,032 tons. GrcatBritain exports crudes worth$2, 073, 000,
and intermediates worth $156,000. British imports of both classes—
but chiefly intermediates — are valued at $758,000.
As already noted, nearly all the intermediates employed in manu-
facturing coal-tar dyestuffs in the United States come from Germany.
This is also the case for Belgium, the Netherlands, and Russia, and
very largely so for France.
Briefly stated, Germany makes three-quarters of the world's arti-
ficial dyes and controls the supply of raw material for one-half of the
remaining quarter. Furthermore, for one great class of dyes, the aliza-
rin colors, and for a vast number of minor subdivisions, that country
is almost the sole source of supply. It possesses in an exceptional
degree a well-known commercial power to influence if not force
customers requiring a large variety of dyestuffs to purchase from it
all the entire stock needed. The industry is in such a position that it
can easily render almost impossible in a given country the production
of intermediates or finished dyes, unless prevented by governmental
protection or assistance.
The exceptional position of the Swiss industry is due to the fact
that it started simultaneously with the German industry, and kept
even step with its more powerful neighbor in the different stages of
evolution. There are very friendly relations between the leaders in
DYESTUFFS FOB AMERICAN CNDUSTEIES. 33
the two countries. The bulk of the Swiss production is at Basel,
on the German frontier. The Swiss industry depends chiefly on
Germany for its intermediates and for its heavy chemicals; at the same
time it does not threaten the supremacy of the German dyestuff trade
in the world's markets.
CAUSES OF GERMANY'S SUPREMACY.
The actual supremacy of Germany in the production of coal-tar
dyes has been outlined above and its dominating position in inter-
national commerce clearly shown. It remains to describe how this
supremacy has been won and how it is maintained.
The base of the present structure was laid half a century ago
When the industry of artificial dyes tuffs was still in swaddling
clothes. A remarkable number of German chemists of the first
rank and of the second rank were attracted to the new industry.
The admirably equipped laboratories of the German universities and
schools of science were devoted largely to research in the new field.
Simultaneously, in Germany, the molecular constitution of the aro-
matic hydrocarbons was revealed by Kekule, and a vast amount of
scientific knowledge, keen mental effort, high inventive capacity, and
patient labor was devoted to applying the new theories to the dis-
covery of tinctorial compounds among the derivatives of the aro-
matic series. A small army of plodding, but still clever, young
chemists carried out thousands and thousands of separate researches
under the leadership of brilliant men, such as Hoffmann, Bayer,
Liebermann, Graebe, Witt, and many others. Far more was done in
Germany to develop the possibilities in the province of synthetic
dyes than in all the rest of the world. At the same time the young
industry was fortunate in securing the generous cooperation of finan-
ciers with farsighted courage and technical managers of exceptional
sagacity. What is said of Germany is also essentially true of Swit-
zerland but naturally on a more modest scale. The seventies saw
the industry well defined and established upon a solid basis, while
the progress of discovery continued at an increased rate. The
notable triumph of this period was the introduction of synthetic
alizarin. During the eighties there was an increased appearance of
new classes of important dyes. It was the golden decade. The
industry was recognized as one of the great national assets of Ger-
many. In the nineties there was a decided lull in invention. Great
attention was devoted to the standardizing of manufacture, and espe-
cially to the organization of the foreign trade. Germany became
practically independent of the world in regard to its supply of coal-
tar crudes. The relations between the great manufacturing houses
became cordial, and there was a general spirit of cooperation. The
manufacture of a large number of valuable medicinals and photo-
graphic chemicals from coal-tar intermediates was added to the pro-
duction of dyestuffs. Great quantities of these intermediates were
also employed in the preparation of high explosives. All this con-
tributed to making the industry better balanced and more symmetric,
while, of course, adding to its complexity.
The present century has seen a steady development. Synthetic
indigo won its great victory. The discovery of new types of colors
has become rare. Close trade agreements have come into existence,
34 DYESTUFFS FOR AMERICAN INDUSTRIES.
with Government approval, and have been maintained without
difficulty. At present the industry is the most remunerative in the
Empire, and the one most conspicuous in international trade as
distinctly and predominantly German. It has been created in
Germany, and is regarded by Germans as their most brilliant triumph
in applying science to industry. The rest of the world generously
recognizes the full right of Germany to be justly proud of its accom-
RESEARCH THE CHIEF CAUSE.
Unquestionably the chief factor in favoring the early start of the
industry and its remarkably rapid and harmonious development
was the spirit of research in Germany and the marvellous equipment
for facilitating, largely at public expense, the exercise of this spirit.
While other countries sought to encourage the introduction of new
branches of industry by the aid of tariff protection, in Germany
manufacturers, capitalists, and Government officials early recognized
the creative power and earning capacity of highly organized industrial
research. Any marked advance in developing the coal-tar chemical
industry in the United States must depend upon the full recognition
of this fact, for no other industry is so intimately associated with
research of the highest scientific character.
A most competent authority, Dr. B. C. Hesse, says in this connec-
What we do need is a semimanufacturing laboratory in which to ascertain the most
favorable conditions for carrying out those operations which the work of the Germans,
both in their patents and in their commercial exploitation of them, has shown to be
needful or worthy of prosecution. That, however, is no child's play task; it calls for
engineering skill of the highest order, chemical knowledge of great refinement, and
experimental ability of high rank. Much will have to be learned and determined as
to the proper materials of construction, the proper size and shape of the apparatus, and
the most favorable working unit, which is by no means constant from one dyestuff or
one intermediate to another. Many dyestuffs can not be made commercially in lots
much greater than 100 pounds; others can be made in lots of 1 ton, but the manufac-
turing unit, as a rule, is small.
GERMAN INDUSTRY, CAPITAL, DIVIDENDS, ETC.
In analyzing the organization of the German dyestuff industry, it
will be found that not only a vast amount of brain effort has been
expended in its creation but that also the cash investment has been
There are now 22 German establishments devoted to the manufac-
ture of coal-tar colors. Of these 21 are owned by joint-stock com-
panies. The combined capitalization of the 21 companies, in 1913,
was $36,700,000. In that year they paid dividends amounting to
$11,600,000, or 21.74 per cent of the nominal capitalization.
The explanation of this high percentage lies in the fact that for
many years the industry has regularly devoted a large share of its
profits to writing off the real estate and plant accounts and to new
construction. One of the oldest and strongest companies has a
capital of $13,100,000. Its stock sells at 600. In 1913 its net profits
were $6,000,000, nearly one-half of the capital. One-third of this
sum was devoted to a sinking fund for the erection of new plants, etc.,
and to welfare funds for operatives. From the remainder a dividend
DYESTUFFS FOB AMEEIOAN [NDUSTMES. 35
of 28 per cent was paid. This course lias been pursued for so many
years that it is now estimated that at least $ 100, 000, 000 have been
invested in the industry.
It is worthy of note that the next most remunerative chemical
industries in Germany are those devoted to explosives, glass, heavy
chemicals, metallurgy, soap, and candles. The factories number 25'i.
Dividends range from 1 1.2 to 11.8 per cent. Most of the remaining
chemical industries in the Empire pay dividends of 5 to 10 per cent.
It is easily seen that financially the German coal-tar dye industry
is exceptionally well fortified and in a position to resist powerfully
any attempt to destroy its supremacy.
GEOGRAPHY OF THE GERMAN INDUSTRY.
A marked feature of the industry is its concentration. The plants
are all located within an area forming a square, wdth sides of 300
miles. The actual concentration is even more pronounced, for,
with the exception of the big v T orks at Berlin, all the leading estab-
lishments, as well as the coke fields supplying the tar and the benzol,
are situated on the Rhine and its tributaries, in a narrow strip of
territory less than 200 miles in length. This means cheap haulage
for the bulkier raw materials and facilities for the economical dis-
tribution of finished products by water to all parts of the world.
If an industry of this size in the United States, doing an extensive
trans-Atlantic business, were located chiefly along the banks of the
Hudson, between Albany and New York, and* obtained most of its
raw material and fuel supply within short distances from the river,
the concentration w^ould be practically the same. These conditions
are readily seen in the accompanying map.
RELATIONS BETWEEN COMPANIES.
The advantages of this close concentration, permitting easy com-
munication and transfer of products between different factories, are
intensified by the close relations between the several companies.
Three of the largest organizations are closely allied; three other
powerful companies form another combine. The relations between
the two big units are, however, friendly, and this is the case also
with the relations between the larger and the smaller firms. There
is keen competition to maintain high standards of excellence in
products and to dimmish the cost of production, as well as to bring
out new dyestuffs; but there is a well-organized combination to
maintain prices and to render mutual assistance in utilizing inter-
mediates and by-products. For practical purposes the industry is a
unit, especially in all that concerns its dealings with foreign markets
and with foreign attempts at competition. These trade agreements
and cooperative arrangements seem to have prevented the appear-
ance of rivals on German soil during recent years. They have made
themselves frequently felt on this side of the ocean, as efforts have
been exerted from time to time to secure emancipation from de-
pendence upon German intermediates or finished products.
DYESTUFFS FOR AMERICAN INDUSTRIES.
DYESTTTFFS FOB AMERICAN [NDUSTRIES. 37
EQUIPMENT OF PLANTS.
As the genera] industry lias developed, the individual companies
have, in several cases, widely extended their operations, so as to
manufacture all or nearly all of the intermediates required in their
processes and a Large share of the beavy chemicals needed. They
nave gone outside the limits of color chemistry and manufactured
a variety of synthetic medicinal preparations, several synthetic per-
fumes, and some important photographic chemicals, as well as mater-
ials for modern high explosives. Tins has meant a great diversity
of equipment and a delicate adjustment of manufacture, so as to
permit the complete utilization of all by-products. In this respect
the coal-tar chemical industry shows a marked resemblance to the
great American packing industries. Starting with 10 crude coal-tar
compounds, it produces a host of valuable articles, but finds methods
of utilizing and deriving profit from all its by-products. If any such
compounds occur in the evolution of a new product, and threaten
waste and loss, they are transformed into other new preparations,
for which uses can be created.
All of this involves extended application of chemical engineering,
and means the employment of a wide range of technical devices.
A couple of examples may be cited as showing the extensive plant
and staff and output of German works and the rate of expansion.
The famous ''Farbwerke" at Hochst started in 1863 with 5 work-
men, making the few aniline dyes then known. By 1888 it employed
1,860 workmen and 57 chemists, and utilized 1,840 horsepower in
its steam engines. It then produced 1,750 different colors. In
1912, 30,000 horsepower were required. The staff included 7,680
workmen, 374 foremen, 307 chemists, and 74 engineers. Wages
amounted to $2,050,000, and salaries and bonuses to $1,240,000.
The number of colors reached 11,000. Synthetic alizarin and indigo
were leading products, and such materials as antipyrine, tuberculin,
and diphtheria serum were made on a large scale.
A still larger establishment is the Badische Anilin- mid Soda
Fabrik, near Mannheim on the Rhine. It covers about 500 acres,
with a water front of a mile and a half on the Rhine. The buildings
cover 100 acres. Transportation between the several hundred build-
ings is effected by 42 miles of railway. Power is generated and
transmitted by 158 boilers, 386 steam engines, and 472 electric
motors. Steam fire engines number 25, and there are 400 telephones.
Each day there is a consumption of 1,000 tons of coal, 40 tons of ice,
40,000,000 gallons of water, and 2,500,000 cubic feet of gas. In
1908 workmen numbered 8,000, chemists 217, engineers 142, and
the commercial staff 918.
WAGES IN THE GERMAN FACTORIES.
The participation of labor in the cost of finished dyes is not high.
It ranges from 10 to 15 per cent, and is usually nearer the lower
figure. There has been, however, a steady increase in the average
wage rate of late years. The average daily wage in Germany for
all labor — boys, and common and skilled labor — was $0.65 in 1886.
In 1908 it had reached $1.14, an increase of 77 per cent. In 1906 the
average daily wage hi the Badische works for a 10-hour day was
$1.04. To the normal wage should be added the contribution by
38 DYESTUFFS FOR AMERICAN INDUSTRIES.
employers to the State old-age, accident, and sick funds, bonuses
gained by many workmen, and the gifts for general welfare. In the
case of the Badische this gift was $750,000 in 1908. Including
these various items, it may be assumed that the prevalent adult
daily wage in the dyestuff works is now about $1.80, as far as the actual
outlay by the employers is concerned.
A large item in the cost of production is due to the salaries of
well-trained, competent chemists and engineers, who supervise every
step of the multitudinous processes. Thus, the " Badische" employs
30 well-equipped chemists — university graduates — in the research
laboratory alone, quite apart from the manufacturing staff.
PROCESSES OF MANUFACTURE.
The chief processes employed in transforming the 10 coal-tar
" crudes" into nearly 300 intermediates required for the direct pro-
duction of dyestuffs are 11 in number. Slightly varied in individual
cases, they constitute the great bulk of the operations performed in
color works. They are of such fundamental importance that a
brief description is desirable in order to bring out clearly the high
degree of correlation and coordination that characterizes the in-
dustry. These processes are (1) nitration, (2) chlorination, (3) sul-
phonation, (4) reduction, (5) oxidation, (6) caustic fusion, (7) alkyla-
tion (8) liming, (9) condensation, (10) carboxylation, (11) diazo-
tizing and coupling.
(1) Nitration. — An aromatic compound is treated with a mixture
of nitric acid and sulphuric acid. As a result usually one, but some-
times two or three, atoms of hydrogen are replaced by the nitro
group, N0 2 . The extent and nature of the reaction are largely
effected by the factors of time, temperature, and proportions. Usu-
ally the residual, somewhat diluted, sulphuric acid can be concen-
trated and used repeatedly.
(2) Chlorination. — Action of dry chlorine gas. The gas is usually
obtained in connection with the electrolytic production of caustic
soda from salt, is liquified for transportation, and allowed to vola-
tilize as needed. The reaction is not so easily controlled as nitration
and a variety of substitution products are often the result, causing
much difficulty in separation. One-half of the chlorine employed is
recovered in the form of hydrochloric acid. The synthetic produc-
tion of indigo involves the use annually of over 5,000 tons of chlorine,
prepared simultaneously with nearly 6,000 tons of caustic soda, and
yielding, as by-product, nearly 8,000 tons of 33 per cent hydro-
(3) Sulplionation. — The action of fuming sulphuric acid, usually in
very large excess, to act as a vehicle. The reaction is, in a few cases,
easily controlled. In most instances a variety of sulpho-acids are
obtained, requiring separation, and involving the problem of utiliza-
tion. The excess of sulphuric acid is generally lost.
(4) Reduction. — The substitution of hydrogen for oxygen in nitro-
compounds, forming the corresponding amido-bodies. Thus, benzol
is changed by nitration to nitrobenzol and that, by reduction, to
amidob.enzol, or aniline. Iron filings or turnings, with acetic or
sulphuric acid, form the usual reducing agents. The resultant iron
salts are without value.
DYESTUFFS FOR AMERICAN INDUSTRIES. 39
(5) Oxidation. — Potassium bichromate, potassium chlorate, lead
peroxide, manganese dioxide or a permanganate, with hydrochloric
acid or sulphuric acid, are the usual reagents. The residues, chrome
alum, potassium chloride, etc., arc all susceptible of utilization.
(6) Caustic fusion. — The operation is performed chiefly with
sulpho-acids. As a result the sulpho-group is replaced by hydroxyl.
Thus benzol monosulpho-acid, on fusion with caustic soda, gives
phenol, or carbolic acid. The residue of sodium sulphite is some-
times used in making bisulphite, more often discarded. The oper-
ation is one requiring unusual care, and the results are often variable.
(7) AlTcylation. — -The introduction into hydroxyl or amido groups
of the radicals methyl or ethyl, present in wood alcohol and gram
alcohol. The alcohols, or methyl or ethyl chloride, are used, along
with hydrochloric acid, and the operation is effected at elevated
temperatures under pressure in autoclaves.
(8) Liming. — The use of lime or chalk to effect separations in
mixtures, especially of sulpho-acids, through the differing solubil-
ities of the calcium salts. Sometimes the purpose is to decompose
chlorides and effect the separation of resultant acids and aldehydes.
(9) Condensation. — A large class of operations in which two mole-
cules of the same substance, or of different substances, unite to
form a new compound, with the elimination of water, or ammonia,
or hydrochloric acid. Sulphuric acid in considerable excess is the
usual condensing agent. When used it reappears as a spent acid,
too weak to admit of profitable recovery. Other condensers are the
chlorides of zinc, aluminum, antimony, sulphur, and phosphorus.
In most cases they can be recovered at slight cost and used repeatedly.
(10) Carboxylation. — The introduction of the acid carboxyl group,
by the joint action of caustic soda and carbon dioxide on phenol and
its homologues. Thus phenol gives salicylic acid; a-naphthol gives
oxy-naphthoic acid. The alkah is recovered in the form of chloride
(11) Diazotizing and coupling. — An aromatic amine reacts with
nitrous acid, forming a diazo-compound. Thus aniline yields diazo-
benzol. Such a diazo-compound. in the presence usually of sodium
acetate unites readily with a variety of aromatic substances; the
operation is termed coupling. The product of such a reaction splits
up, yielding the original amine and the amido-derivative of the
second substance employed. Thus, salicylic acid, by coupling with
a diazo-compound and subsequent reduction, is changed into amido-
salicylic acid, an intermediate of widespread use. This sequence of
reactions is of prime importance. It serves to produce a variety of
intermediates, and is the fundamental operation in the manufacture
of the so-called azo dyes, which constitute about one-half of the
number of artificial dyes now current in the world's trade.
The purely chemical transformations fail to reveal the full extent
of the sequence of operations in eventually obtaining intermediates
from crudes by a chain of reactions. Between any two successive
chemical changes there are from one to three mechanical operations,
such as baking, boiling, filtering, precipitating, blowing off with
steam, and the like. There are also minor chemical operations,
such as the change of acids or bases into salts; the separation of salts
from liquids; their purification, drying, and storing, etc.
DYESTTJFFS FOE, AMERICAN" INDUSTRIES.
In the preparation of about 300 intermediates by the use of these
11 classes of reactions there is encountered the greatest diversity of
problems to be handled. Every step involves the production of
compounds other than the one mainly sought. How to limit their
appearance so far as possible, how to utilize them when inevitably
formed, how to adjust and balance the consumption of all the prod-
ucts, are problems that demand exceptional technical and business
ability and the closest cooperation between the manufacturing and
the commercial staffs of an organization.
UNIFORMITY OF PRODUCT.
One of the most serious demands on the technical staff of a dye-
stuff factory is the necessity of obtaining the highest uniformity in
finished products. Standards of purity are now very rigid. Pur-
chased dyes are subjected to severe tests. This means great refine-
ment and exactitude at every stage of the process in the evolution
of a dyestuff. Exhaustive and careful tests are essential at each
step before an intermediate can be submitted to a new chemical
transformation. The margin allowed for variation from the standard
of purity is very slight. In some instances the presence in a given
intermediate of as little as one-fifth of 1 per cent of a closely allied
compound, formed simultaneously in its production, would be pro-
hibitive to its further use.
All of this adds to the complexity of the manufacturing problem.
In fact, at every stage the artificial-dyestuff industry presents a
marvelous maze of materials and operations, interdependent and
closely interlocked technically and economically.
The astounding complexity of the manufacture as a whole has re-
cently been set forth in a very striking and clear manner by Dr. B.
C. Hesse, in comprehensive presentations of the entire series of opera-
tions involved in the production of certain classes of dyes. With
his permission summaries of some of the more striking phases of
manufacture, as admirably outlined by him, are presented.
The current types of dyes now number 921. Each one, as a rule,
is offered commercially in a variety of brands, differing minutely
from each other in exact shade, or in the availability for use with
certain textiles. There are thus many thousand distinct brands for
These 921 dyes are divided into 17 separate chemical classes, as
shown in the table that follows:
Classes of dyes.
Alizarin and anthraquinone
Tri- and di-phenylmethane .
Oxazin and thiazin
Classes of dyes.
Nitro, nitroso, auramine, chinolin, thio
benzyl, and indophenol
DYESTUPFS FOB AMKlilt'AN INDUSTRIES. 41
ALIZARIN, NAPIITIIOL YELLOW, MAGENTA.
Some of the simpler types of production may first be presented.
Crudes, intermediates, and final dyes are distinguished by capitals.
Operations are in parentheses.
Sequence of operations in alizarin manufacture:
(fusion with caustic soda and chlorate)
. There are here only three chemical transformations. The anthra-
quinone serves also as the starting point for a variety of important
dyes. Alizarin has been the source of a vast amount of wealth to
Germany since its discovery in 1869, when it began to supersede
madder. The patent rights expired in 1886, but its manufacture
has never been attempted in the United States.
Operations in manufacture of napliiliol yellow:
(fusion with caustic soda)
This is one of the earlier standard dyes. Patent rights expired in
1897. Some has been manufactured in this country from imported
a-naphthol trisulpho-acid, the last transformation being compara-
tively easy. Practically none is made here.
42 DYESTUFFS FOR AMERICAN INDUSTRIES.
Operations in manufacture of magenta:
(reaction with o- and p- toluidine, and o- and p- nitrotoluol)
(treatment with hydrochloric acid)
Preparation of nitrotoluol and toluidine:
o- and p- NITROTOLUOL
o- and p- TOLUIDINE.
Magenta is a dyestuff largely used in the United States. It is
made here to some extent, but the manufacture is confined to the
final step, the action of hydrochloric acid on the magenta base. In
$1,000 worth of magenta the hydrochloric acid participates to the
extent of about $5.50.
HYDROQUINONE AND SYNTHETIC INDIGO.
Following are the operations in the manufacture of Tiydroquinone:
Hydroquinone, while not a dye, is used in great amounts as a
photographic developer, and is an important accessory product of
German factories. It is made to some extent in the United States
from imported or domestic aniline.
DYESTUFFS FOB AMERICAN [NDUSTEIBS. 43
There axe four methods of making indigo. Three start from benzol
and the fourth from naphthalene.
(treatment with chlor-acetic acid)
(fusion with sodium oxide)
The crucial point in the sequence is the transformation of phenyl
glycine into indoxyl. An older method used fusion with caustic soda.
The yield was about 45 per cent. A later process made use of sodium
amide, with nearly quantitative results. A still later process substi-
tuted advantageously sodium oxide for the amide.
The manufacture from naphthalene is slightly more involved:
(action of ammonia)
(action of sodium hypochlorite)
(action of chlor-acetic acid)
PHENYL GLYCINE A-CARBOXYLIC ACID
(fusion with caustic soda)
The development of this industry illustrates the influence of quan-
tities. This last method was the first to be used successfully on a
commercial basis. This was due primarily to the fact that at that
time, by fusion with caustic, 90 per cent of the phenyl glycine com-
pound could be changed into indoxyl. It was also largely due to
the fact that naphthalene could be had in abundance, and was seek-
ing a market. Pure benzol could be secured, but the preparation of
44 DYESTUFFS FOR AMERICAN INDUSTRIES.
the vast quantity of pure benzol needed for the world's consumption
of indigo would have entailed the simultaneous production of a very
large amount* of toluol, for which there was at the time no visible
demand. Naphthalene could be employed without involving the
production of other coal-tar crudes. Gradually new uses for toluol
have been found, and more and more pure benzol is available at low
rates. Probably the manufacture of indigo will soon be based
entirely upon the use of benzol as the primary material.
The history of this manufacture illustrates how intimately com-
mercial conditions control the choice of materials in the dyestuff
industry, and how in all branches a certain "balance of power" must
be maintained in order to assure the highest economic results. It is
interesting to note that the first step in the naphthalene process
involves the use of sulphuric anhydride representing the annual con-
sumption of 80,000 tons of 50 per cent pyrites. The chlor-acetic acid
employed represents an annual consumption of 4,500 tons of glacial
acetic acid, and 5,000 tons of liquid chlorine.
THE KETONE DYES.
To illustrate operations on a more varied scale, the group of so-
called ketone dyes may advantageously be summarized. These are
closely related chemically, include representatives from several of
the 17 classes, and show how these classes are interlaced and inter-
locked with one another. The 24 dyes in this group constitute one-
fortieth of the total number of current dyes. They are all good
sellers. Most have been in use 30 years. Eight were never patented
in our country. American patents have expired on eleven, and will
expire on four in the course of a year, and on a fifth in 1925.
The common material employed hi making each of the 24 dyes is
termed "Michler's ketone." It is obtained by the reaction of car-
bonyl chloride on dimethyl aniline. The latter is made from aniline,
aniline salt, and wood alcohol. Aniline, as already noted, is made
from benzol by nitration and reduction of the resultant nitrobenzol.
Carbonyl chloride results from the reaction between carbon mon-
oxide and chloride in the presence of a contact agent, such as plati-
num or animal charcoal. In a current process of manufacture,
calcium chloride, lime, and coke are heated in an electric furnace.
The carbonyl chloride gas evolved is condensed to a liquid at 8° C.
The gas is passed into liquid dimethyl aniline until the weight has
increased 40 per cent. The reaction is completed by heating for
several hours at 100° C. The resultant ketone is a solid, melting
at 174° C.
By using grain alcohol instead of wood alcohol the corresponding
ethyl compound is secured. This is used by preference in a few
In the reaction between carbonyl chloride and dimethyl aniline
21.2 pounds of hydrochloric- acid gas are released for every 100
pounds of ketone formed.
In making dyes by the aid of ketone, "condensation" takes place.
The ketone and another coal-tar derivative react upon each other
in the presence of phosphorus trichloride or phosphorus oxy chloride.
The complex dye results, and hydrochloric acid and phosphoric acid
are by-products. The latter can be changed again into phosphorus
oxychloride for renewed use.
DYESTUtfFS FOR AMERICAN I XhrsTlM I IS. 45
In making 100 pounds of ketone and in using it bo produce dyes,
a total amount of LOO pounds of 33 per cenl hydrochloric acid is
released. Of this about 30 pounds are utilized to prepare sails of
basic dyes produced. The remainder is available for other purposes.
In making and using the ketone, four of the eleven general opera-
tions required in dye manufacture come into play, viz, nitration,
reduction, alkylation, and condensation. The materials employed
are benzol, coke, phosphorus, chlorine, nitric acid, sulphuric acid,
hydrochloric acid, iron filings. Intermediates formed are nitro-
henzol, aniline, dimethyl aniline, carbonyl chloride.
Turning now to the production of the 24 dyes in question, it is
found that 23 final intermediates are necessary. The total number
of operations requisite to produce these final intermediates, starting
in each case from coal-tar crudes, is 118. Derivatives of benzol,
toluol, naphthalene, and phenol appear in the combinations effected.
In 16 cases a single coal-tar crude is represented; in the remaining
cases, two are present. On an average 5 transformations are re-
quired to produce a final intermediate ready to condense with ketone.
Reduction occurs 31 times, nitration 21 times, sulphonation 13 times,
oxidation 12 times, condensation 11 times, etc.
If equal amounts of ketone were used to manufacture the 24 dyes,
using in each case 100 pounds, the total 2,400 pounds of ketone would
produce 4,605 pounds of finished dyes. In this final product different
constituents would participate as follows: Ketone, 52.11 per cent;
benzol, 7.58 per cent; toluol, 5.21 per cent; naphthalene, 11.42 per
cent; phenol, 1.69 per cent; from sulphonation, alkylation, etc., 21.99
per cent. Benzol, however, constitutes 58.21 per cent of the ketone
used, so that the total participation of this hydrocarbon in the dyes
would average 37.91 per cent.
Naturally these 24 dyes are not required by the trade in approxi-
mately equal amounts. In constructing a plant for their manufac-
ture a high degree of intelligence is imperative, in order to avoid
waste of time, space, and apparatus, in planning the size and relative
position of the different buildings.
To effect the 118 operations it is not necessary to have that number
of sets of apparatus. The 11 major operations require, however,
in each case, equipment varying in size, etc., depending upon the
materials to be transformed, their relative amounts, the time for
manufacture, etc. Thus the same apparatus for nitration is not
necessarily adapted for use with both benzol and naphthalene, the
same condensation apparatus is not applicable for all forms of con-
In the manufacture of this group of 24 dyes there are several
instances where operations produce two op more products, usually
isomeric compounds, and the problem of complete utilization is pre-
When chlorine acts upon toluol, three substances, in varying pro-
portions, are always formed — benzal chloride, benzyl chloride, benzo-
trichloride. Benzyl chloride serves in producing 3 dyes, and benzo-
trichloride 1 dye, in the group of 24. Benzal chloride is not utilized
in this group, but it serves as the starting point for the manufacture
of a much larger group — the benzaldehyde dyes. Again in nitrating
toluol, two isomeric products are always formed — orthonitrotoluol
and paranitrotoluol. The latter is used in making one dye of the
46 DYESTUFFS FOR AMERICAN INDUSTRIES.
group in question. The ortho variety is, however, of much greater
general importance. It is the starting point for making tolidine,
the essential constituent in a group of 45 dyes. The use of the para
form in this case, is the utilization of a by-product unavoidably
occurring in another branch of manufacture, with the consequent
avoidance of waste and loss.
The two instances illustrate how the commercial side of the indus-
try must constantly be on the alert to keep all the intermediate
products in alignment, with avoidance of excess production over
market requirements. This merchandizing effort involves infinite
painstaking and highly developed skill.
The group of 24 dyes includes 15 acid and 9 basic products. Fur-
ther, 7 are used on cotton, 11 on silk, 17 on wool, and 5 more on
wool with the aid of the chrome process. One is employed in calico
printing; another is largely used for paper, leather, jute, artificial
silk, coconut fiber, and lakes.
As a whole, this group, although involving such a measure of inter-
locking and interdependence, as shown in the accompanying chart,
presents the simplest and least intricate series of relationships in the
industry. Other groups show much greater complexity, chemically,
technically, and commercially.
A larger and more complex group is that of the benzidine dyes,
numbering 82. The common constituent here is benzidine, a benzol
derivative. The formation is as follows:
(fusion with caustic soda and zinc dust)
(action of nydrochloric acid)
Like Michler's ketone, benzidine itself is not a dyestuff. It is only
in combination with other coal-tar derivatives that it gives rise to
color products. In order to effect any such combination the benzi-
dine is first changed by the action of nitrous acid into its tetrazo
derivative. In this form it reacts with some 44 intermediates to
produce 82 current dyes. These 44 final intermediates are derived
from benzol, toluol, xylol, phenol, cresol, and naphthalene. Their
preparation calls for the production of 55 other intermediates, not
used for direct reaction with tetrazobenzidine. The derivation is:
Benzol 10, toluol 2, xylol 1, phenol 1, cresol 2, naphthalene 28.
In combining benzidine with the 44 compounds, to produce the 82
dyes, the latter are used two at a time, three at a time, four at a
time, or each one twice. Evidently, from the possible permutations
and combinations, a host of differing tinctorial products can be de-
rived from the 44 final intermediates. Of the multitude, but 82
have won a recognized position in the field of dyeing.
in ESTUFFS FOB \ M ERICAH [NDUSQ BIES.
J ~ ';
48 DYESTUFFS FOR AMERICAN INDUSTRIES.
The average number of transformations required to make final
intermediates from naphthalene is 4.5, from the other crudes 3. As
the operations requisite to prepare tetrazobenzidine and its final
reaction with one to four intermediates are 5 in number, the total
number of chemical changes involved in the manufacture of benzi-
dine dyes ranges from a minimum of 6 to a maximum of 23. The
interdependence is illustrated by the two accompanying charts.
Benzidine dyes are of prime importance, as they dye cotton di-
rectly without the use of a mordant. The range of colors and shades
is, however, inadequate to meet the demands of cotton dyers.
TOLIDINE AND ALLIED DYES.
In order to fill in the lacking tints, recourse is had to tolidine,
dianisidine, and five other less important derivatives of benzidine.
Together these yield the 167 direct cotton dyes, of the so-called
diphenyl type, now in current use. They are divided as follows:
Benzidine 82, tolidine 43, dianisidine 28, a-nitrobenzidine 1 , dichlorben-
zidine 3, benzidine-monosulpho-acid 2, benzidine-disulpho-acid 4,
These complementary substances are used exactly as benzidine
itself, reacting in the same way with the 44 final intermediates
already mentioned. They require, however, for the production of
several current dyes, a number of additional finished intermediates,
more or less complicated in their relationship. They react also di-
rectly with phenol and cresol.
Tolidine is made from o-nitrotoluol in the same manner as benzidine
is prepared from nitrobenzol.
Together, the dyes of the ketone, benzidine, tolidine, etc., types
form about one-fifth of the current artificial colors.
PATENTS IN THE GERMAN INDUSTRY.
Patents have been multitudinous in connection with the evolution
of the German coal-tar dyes tuff industry. From 1876 to 1912 they
numbered 8,062, or 224 annually on an average. Many correspond-
ing patents were taken out in other lands, especially in France and
Great Britain. The number in the United States was 2,432.
But very few of the important intermediates have been patented.
Not a few dyestuffs have been patented by non-German inventors.
Most patents cover a vast range of possibilities, and protect the
manufacture of thousands of theoretical dyestuffs, of which an infini-
tesimal number ever win a place in the world's markets. It is
claimed with authority that not over 1 per cent of the German
patents in this industry have ever proved remunerative. In the case
of the 921 dyes in current use at the beginning of 1913, 762 German
patents were involved. Of these, 485 were originally patented in the
United States. One-half of the American patents have expired.
Many of the remaining patents expire this year or in the immediate
future. Over 50 per cent of the current dyestuffs were never pat-
ented in the United States.
The general situation shows clearly that, as far as patent protection
is concerned, numerous dyes have been patented by non-German
DYESTT FKS FOB AMERICAN INDUSTRIES.
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DYESTUFFS FOR AMERICAN INDUSTRIES.
DYESTUFFS FOB A.MEEICAN [NDUSTRIES. 51
inventors, that many dyestuffs bave never been patented, fchat the
patents on many others bave expired, a considerable number each
year, since L880. In spite of all this apparent freedom, and fche
absence of all patent protection on the production of the intermediates
requisite for dyestun manufacture, efforts in other countries to chal-
lenge and contest Germany's dominant position in the dyestuff indus-
try have been few, and practically futile.
As a matter of fact, Germany has demonstrated her ability to
outrank the entire world in making patentable compounds from
nonpatented intermediates and, in addition, to manufacture these
intermediates in open competition with all rivals.
In its ultimate analysis, the situation shows that German chemists
and captains of industry have actuaUy done the bulk of the hard and
complicated labor inherent in the creation and organization of a
vast branch of manufacture, and that they have not hesitated to
use the power associated with its hardly won national predominance
to prevent effectively any serious competition in industrial lands.
AMERICAN ATTITUDE TOWARD THE GERMAN INDUSTRY.
The incmiry why the natural resources of our country have never
been utilized on any extensive scale to meet the needs of American
consumers and create a distinctly American coal-tar chemical industry
has often been raised.
The few American manufacturers of artificial dyestuffs claimed that
they were doing all that was possible under existing economic and
fiscal conditions. Consumers of dyestuffs were, as a rule, indifferent,
satisfied to receive regularly a supply of all needed colors, ordinarily
uniform in strength and meeting every possible requirement in shade
or adaptability to fabric and material. American economists dwelt
upon the enormous complexity of the problem, bristling with diffi-
culties at every step, shoidd any attempt be made to dispute the
supremacy of the foreign industry, intricate and complicated beyond
any other organized field of human effort and formidably intrenched
within the limits of a single powerful nation.
No direct, concrete attempt was ever made to focus national
thought in the United States upon the problem, to enlist the coopera-
tion and combined effort of producers of crude products, actual or
potential manufacturers of finished dyes, the many trades consuming
dyestuffs in quantity, the still more numerous branches dependent in
turn upon them, and the general industrial world in seeking an
effective solution worthy of the nation's rank.
The present crisis in the world's affairs, threatening to interrupt
any day the customary supply of artificial dyestuffs, has served to
awaken general attention to the importance of this national question
to a degree never attained by the more or less academic discussions
of the past. A famine in dyestuffs strikes at the very existence and
profitable continuance of a large group of industries. American
chemists have been put in the position 01 defending themselves, and
explaining why they could not, at once, meet the Nation's need in an
52 DYESTUFFS FOE AMERICAN INDUSTRIES.
PRODUCERS OF COAL-TAR CRUDES.
Those in control of our coking interests, and controlling the coal-tar
branch, are thoroughly sympathetic to any prospective enlargement
of the demand for coal-tar crudes. Recovery plants for benzol and
tar in coke works will be rapidly increased, tar distilleries will erect
the requisite plant for an ample supply of the requisite 10 coal-tar
crudes, just as soon as there is the fairly permanent assurance of a
regular demand for the products.
MANUFACTURERS OF HEAVY CHEMICALS.
These likewise are thoroughly in sympathy with the creation of a
large industry, capable of using great amounts of staple chemicals.
There does not seem to be any inclination on the part of such man-
ufacturers to embark themselves in the production of dyestuffs.
There is, however, a distinct readiness to cooperate, by organizing,
on a modest scale, the manufacture of the leading intermediates.
One firm has ventured to erect a somewhat extensive plant, after
successfully establishing the manufacture of a few intermediates. of
recognized purity. The feeling here is, however, conservative.
There is a marked disinclination to invest considerable amounts,
while the danger is present of awakenmg sooner or later the determi-
nation on the part of the German industry to throttle any too am-
bitious attempts by effective and persistent selling at prices under
cost. With the assurance of adequate legislative protection against
the danger of " dumping" on the part of foreign producers of coal-tar
intermediates, there is every indication that existing chemical indus-
tries would embark readily and extensively in the production of this
class of compounds.
Hydroquinone, the well-known photographic developer, falling
practically in this category of coal-tar compounds, although not used
in the production of colors, is now successfully manufactured by an
American chemical firm.
MANUFACTURERS OF ARTIFICIAL DYESTUFFS.
In this class there is no question of a readiness to advance far
beyond the modest limits of the present manufacture as soon as
adequate legislation is assured. The manufacturers assert that 90
per cent, by value, of the artificial colors used in the United States are
now unprotected by patents, or will be freed from patent protection
within two or three years; and, further, that practically all of the
genuine needs of American colorists are covered by this 90 per cent
With the protection of an effective antidumping clause, they feel
that much can be done toward building up the dyestuff industry in
our country. The manufacture of the simpler intermediates, and
of finished dyes involving a minimum of chemical transformations,
could be attempted with a degree of security and confidence now
The certainty that ruthless and prolonged underselling on the part
of foreign competition could be effectually forestalled would
undoubtedly stimulate effort in several directions and aid in gradually
building up important features of the industry, even if there could be
DVKSTUFKS FOK AMERICAN [NDUSTBIES. . r ).'i
no attempt at creating a self-contained, national, dyestuff industry
in the Immediate future, [nstances are cited where such an exten-
sion of the range of manufacture of intermediates and of finished
dyes would unquestionably take place. Among these are such
important intermediates as nitrobenzol, aniline oil, and salts, resorcin,
nitrophenol, salicylic acid, benz aldehyde, phthalic acid, the naphthols
and the naphthylamines. Among the finished dyes are a variety of
colors obtained by not more than two transformations from the
There is some feeling, in this connection, among our dyestuff manu-
facturers that the patent laws could advantageously be modified, so
as to assure the working on American soil of all patents granted by
our Government. Great Britain has lately made changes in this
direction in her patent laws. Germany has for years required that
the owners of a patent must work the invention to an adequate
extent in the Empire or do all that is necessary to secure such working.
Otherwise, if deemed needful in the public interest, permission is
granted others to use the invention. The owner of the patent receives
adequate compensation, and the manufacture in Germany is assured.
It is claimed that if such legislation had been in force 30 to 40 y^ars
ago, when invention in the dyestuff industry was at its height,
European patentees would have been forced to build branch factories
in the United States. These factories would undoubtedly have
developed other products. While not helping the then existing
American factories, a large dyestuff industry would inevitably have
been created on American soil, with resultant benefit to the country
The general opinion among American chemists and inventors
in this field is antagonistic to such legislation. Its evils, it is claimed,
more than counterbalance the advantages. Certainly in England
it has not aided in the development of the artificial-dyestuff industry.
CONSUMERS OF ARTIFICIAL DYESTUFFS.
The great textile branches and the other branches consuming large
amounts of dyes tuffs have been indifferent or lukewarm in the past
to the question of an American color industry. Now that their
normal manufacture is threatened by dislocation, they are more keenly
alive to the vital character of the subject. The chairman of. the
dyestuffs committee of the National Association of Finishers of Cotton
Products, A. L. Lustig, lately stated in this connection: "The textile
finisher would have to sacrifice temporarily in some directions in order
to accomplish the greatest good for all, which would be a gradual
development of the coal-tar chemical industry in the United States.
I feel that it would be good business judgment on our part to bear
additional financial burdens for some years to come in order to help
to establish an American coal-tar chemical industry and in this way
ultimately benefit ourselves."
Mr. Lustig is strongly of the opinion that by cooperation between
the American manufacturing interests and the German color makers
much could be accomplished, that we could gain years of time, save
large sums of money, and establish the industry under the most
favorable conditions. He adds: " The German people will require all
their financial resources to repair the damages caused by the present
54 DYESTUFFS FOR AMERICAN INDUSTRIES.
war; but they can furnish us with patent licenses and with some ex-
perts, which would form a nucleus for the elaborate steps needed to
work out this problem. I believe that by the resulting cooperation
with the European manufacturers who, at the proper moment, might
be induced to enter this field, we could help to establish the industry
here, and in this manner prevent a recurrence of the conditions
which jeopardize textile interests at the present time; this might be
done irrespective of material changes in our patent laws, changes of
Some consumers of dyes in quantities, and absolutely dependent
upon certain colors unobtainable at present, have erected emergency
plants and produce the needed dyes at some considerable increase
in cost. In one such case the experiment has worked so well that
the manufacturing company has expressed its readiness to embark
extensively in the industry and enlarge steadily its present modest
plant, if sure of the needed legislation generally demanded.
There is a distinct dread on the part of some users of dyes in regard
to identifying themselves with any concerted move to favor the estab-
lishment of an American dyestuff industry. They state frankly that
any such action would probably result in their being promptly
blacklisted by all importers of colors and cut off from any supply of
dyes, outside of the limited American product.
There is a growing feeling among American economists that the
time is ripe for reaching a decision whether the United States is ever
to have a coal-tar chemical industry, self-contained and independent,
utilizing the great natural resources and meeting the Nation's needs,
as fully as is the case with our iron and steel industry or a score of
other prominent phases of national activity. It is pointed out with
force that every year which elapses strengthens relatively and abso-
lutely Germany's predominance in this field and multiplies in geo-
metrical ratio the difficulties to be overcome should the attempt
ever be made to create the fully equipped American industry. There
seems to be no doubt in the minds of some American economists
that the task can be accomplished, and that the present world's con-
juncture offers the most favorable opportunity for taking the initial
and fundamental steps. The enactment of legislation to prevent
"dumping" would unquestionably give an enormous impetus to
American enterprise and capital, already attracted to this field. But
some years must inevitably elapse before a scientific and technical
staff could be thoroughly trained and before such captains of industry
could be evolved, as in our iron, steel, petroleum, electrical, and other
great industries, peers of their foreign rivals, and often recognized as
AMERICAN CHEMICAL SOCIETY, NEW YORK SECTION.
To meet a widespread demand for explanation, a committee was
appointed by the New York section of the American Chemical So-
ciety to report upon the situation. This committee was composed of
the following members: J. B. Herreshoff, representing the manu-
facturers of heavy chemicals; I. F. Stone, representing manufacturers
of coal-tar colors; J. Merritt Matthews, representing the textile inter-
DYESTUI'TS FOR AMERICAN INDUSTRIES. 55
ests; II. A. Metz, representing the importers; David W. Jayne, rep-
resenting the producers of crude coal-tar products; Allen Rogers,
chairman of the New York section; and Bernhard C. Hesse, chemical
The findings of this committee were considered on November 9,
1914, in detail, and after discussion the report was unanimously
adopted by the section.
The committee's conclusions were in harmony with the general
expression of opinion on the part of those more closely concerned
with the question, consumers, manufacturers, and others, as just
outlined. Special stress was laid in the report upon the imperative
necessity of adequate legislation to prevent " dumping," or under-
selling, by the present dominant foreign industry before any serious
attempt could be made to materially enlarge the existing scope of
American dyestufF manufacture.
ESTABLISHMENT OF AN AMERICAN INDUSTRY.
The successive steps necessary for the establishment of a self-con-
tained American coal-tar chemical industry, under favoring condi-
tions, have been outlined as follows :
1 . Determination of the American ^demand for dyestuffs. — Statistics
show the total value of our imports of foreign dyes, but they do not
show the exact amounts of each dye consumed in the United States
except approximately for alizarin and indigo. It is necessary to
take a census in order to have the data for planning intelligently the
different phases of a combined manufacture destined to supply the
entire domestic demand, and for so coordinating the various features,
as to secure the highest economy. This is not an easy matter, but
it is indispensable. The information might be secured by a general
communication on the part of American consumers of the average
annual amounts required of each dyestuff. It might be obtained
through a careful collocation of the data contained in consular invoices.
Certainly it will never be communicated by importers.
2. Research laboratory. — All interested parties should unite, pos-
sibly with Federal cooperation, in the establishment of a research
laboratory in which the various chemical, mechanical, and engineering
problems connected with the formation of each intermediate and the
production of each finished dye could all be solved and standardized.
Further, in such an experimental institute the entire coordination of
the industry, on the basis of evenly supplying American consumption,
could be carefully determined.
3. Evolution of the productive industry. — Simultaneously with the
organization of such a laboratory, existing and newly formed fac-
tories could start units of production, beginning with the simpler
dyes, or those involving a minimum of transformations. Gradually
the volume would increase, until finally the entire field would be
covered. The central research laboratory would constantly serve as
a clearing house to plan and provide against waste through improper
coordination; and such cordial trade cooperation as exists between
the component parts of the German industry should be sought for.
At the same time our schools of science would organize special courses
to train up the necessary corps of chemists and chemical engineers to
man the growing industry, exactly as they have done for the exten-
sive dyeing and bleaching industries of our country.
56 DYESTUFFS FOE AMEBIC AN INDUSTKIES.
It would take a decade, possibly less, before the industry could
meet the great bulk of American needs; but it would be distinctly a
national industry. Here and there a minor gap must be filled from
abroad until patent rights have expired. Unquestionably American
inventive genius would be spurred to score successes in the new field,
and patents for new dyes discovered in the United States would be
taken out with increased frequency.
Such, in its more essential features, it is claimed, would be the
sequence of stages in the development of a national self-contained
THE PROBLEM IN ENGLAND AND FRANCE.
Great Britam is a country hi which the artificial dyestuff industry
is much more developed than in the United States. It depends,
however, upon Germany for its supply of colors almost as much as
our own land. It has been cut on entirely for over seven months
from this normal foreign supply. So severely have its textile and
other industries been endangered that the British Government has
deemed it an imperative duty to take the requisite steps to build
up promptly a national coal-tar industry, depending upon national
resources for its raw materials and covering the entire country's
demand, or very nearly so.
On November 27, 1914, the President of the British Board of Trade,
in presenting the subject before the House of Commons, said: "If
we were to go on being dependent in the larger portion of our textile
trade on supplies which Germany has the power to cut off whenever
she pleases, we left the industry in a state of peril, and we should cer-
tainly be lacking in foresight if we were not prepared to take the
steps necessary to put a stop to the entire dependence of what was,
after all, the greatest of our manufacturing industries (i. e., textile
manufactures), on commodities entirely under foreign control."
Since then the subject has been actively discussed by chemical in-
terests, textile and dyers' associations, chambers of commerce, etc.
Some have advocated a reversal of the traditional free-trade policy
of the Kingdom, making a temporary exception in favor of artificial
dyes. Some have proposed active cooperation with Switzerland,
whose dye production could rapidly be enlarged, raw material being
supplied from England. Others favor ample financial aid and close
cooperation on the part of the Government, with the assurance of
adequate protection against unfair competition after the war.
This last policy seems to have the majority of adherents, and has
received Government sanction. On February 8 a definite plan was out-
lined by the Government . It is based upon the formation of a national
company with an initial capital of $10,000,000. The Government
is prepared to advance $5,000,000 at the rate of $1 for every $5 sub-
scribed by the public, and an additional $2,500,000 at the rate of $1
for every $4 subscribed. Government advances receive 4 per cent
interest. The Government will also grant $500,000 for a research lab-
oratory. Further details with regard to methods of protecting the
new industry at the close of the war have not yet been received.
Great Britain uses annually about 20,000 tons of artificial dyes,
with an estimated value of $10,000,000. The domestic manufacture
of d} T es ranges from 3,000 to 4,000 tons, one-half of which is exported.
Nine-tenths of the consumption is of German origin.
DYESTUFFS FOB AMERICAN [NDUSTBIES. 57
Tn France a similar movement lias bees inaugurated to perma-
nently free the country from dependence for its dyestuffs upon
Germany or any foreign source. A group of loading chemists lias
devoted itself for some time past to the details 01 the problem.
Recent announcements in the press state that it has been satisfac-
torily solved, and that henceforth every phase of the industry can
be established upon French soil, using exclusively French crude
materials. Coal-tar products are supplemented to some extent by
residues from the beet-root sugar manufacture.
It appears that numerous American industries are dependent
upon the use of dyestuffs and that artificial dyestuffs have displaced
nearly all the natural dyestuffs; that the American consumption of
artificial dyestuffs has attained an annual value of about $15,000,000,
and of tins only about $3,000,000 worth is supplied by domestic
production, the rest coming mainly from Germany; that since the
war in Europe German makers have not bee'n able to supply the
entire demand, and in consequence prices have risen from 25 to 50
per cent on such dyestuffs as can be delivered; that the supply of
coal-tar dyestuffs throughout the world is completely dominated
by the German industry, Germany furnishing in 1913 about 74 per
cent of the total world's consumption; that the German dyestuff
industry has been chiefly developed by the inventive power of
German chemists, combined with a wealth of technical skill and keen
business management scarcely equaled in the history of any other
branch of manufacture; that in the United States the supply of coal
tar is sufficient to provide all of the crudes required for the manu-
facture of the dyestuffs consumed in the country; that our manu-
facture of heavy chemicals is well developed and able to expand
rapidly and supply all needed chemicals for the production of inter-
mediates and their transformation into finished dyes; that 90 per
cent of the dyes now consumed in the United States are patent-free,
and that the remaining 10 per cent will soon be freed from patent
restriction; that the advance of the American dyestuff industry,
beyond certain limits, is persistently checked and prevented by the
united action of German producers in underselling; and that the
present crisis has evoked deep interest on the part of all concerned —
tar distillers, manufacturers of chemicals, manufacturers of dye-
stuffs, and users of the same, and economists in general — as to how
the problem can be solved.
It appears, furthermore, that some American chemical works and
American manufacturers of dyestuffs are ready to embark capital
and experience in very materially enlarging the present limited scope
of the American coal-tar chemical industry, using American crudes
and intermediates, provided effective legislation is enacted to pro-
hibit dumping and to prevent such action toward control of our mar-
kets by a foreign monopoly as is now prohibited to domestic industry.
Far-reaching efforts appear to have been made in England and
France under Government auspices to free these countries from de-
pendence on any foreign service for their supply of dyestuffs.
SMITHSONIAN INSTITUTION LIBRARIES
3 ^Dflfi DDE^TBh? 7
nmah HD9999.D9U6 1915a
Dyestuffs for American textile and other